In a month with diurnal Cancer rising, activities undergo constant changes.
Pay special attention to the Moon and the aspects it makes during the month as well as when it crosses the 2nd or 8th House (natal, diurnal or transit). To a certain extent, also check the trines and sextiles the Moon does to or from the 2nd/8th.
Here the MO is positioned in the diurnal 2nd House right over my natal PL (ruling the diurnal 5th).
And it will also go over my natal VE and natal AS and make a trine to natal MA on the cusp of the natal 5th
It will also make an Antiscia to transiting ME in Taurus ruler of my natal 2nd House.
So a lot of activities related to money matters.
The opposition JU/SA in my natal 2nd/8th Houses is a reminder to pay special attention to my Income Tax this year.

Biggest win - when the MO by transit having entered the AS was conjunct the transiting 8th House.
11 wins 1 jackpot

As you can see, there are so many possible combinations but when you assemble the pieces of the puzzle together, it starts to make sense in one direction.

This diurnal has diurnal JU on the cusp of the diurnal 2nd and ruling the diurnal 8th in trine to the MO in the diurnal MC. The MO being in my natal 6th indicates some form of monetary recognition from my job or benefits coming from my boss. JU is also transiting in my natal 10th.
The ruler ME is making a Grand Trine with transiting SA in Scorpio and natal ME (ruling my natal 2nd) and JU (ruling my natal 8th). ME/SA says 'competence to form an opinion, to pass judgment' (Witte). I will play on this one later.

10 wins - 2 jackpots
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Not everything is related to winning when you look at your diurnal but you need to find some kind of connection with money (2nd/8th), otherwise flow with what the chart is telling you.

Another interesting question. What if you relocate?
In her book 'The Art of forecasting using diurnal charts', Sophia Mason says:
"In the advanced astrology class in the Valley Forge High School Adult Education program, we experimented with a woman's chart who was born in Paris, France. The ruler of her natal 10th house cusp would soon be squaring the ruler of her natal 12th house cusp. The diurnal chart that we used for France indicated that her boss would enter the hospital in 3 days as her natal 10th house ruler would exactly conjunct her diurnal 10th house cusp and at the same time square the ruler of her natal 12th house. The diurnal chart for Parma, Ohio indicated a hospital entry would be 3 days earlier. Her boss entered the hospital 3 days later on the day her diurnal chart set for Paris.... the diurnal chart for the birth chart is always right on target." (p. 3-4)

This one shows a struggling day but it also helped me understand how the aspects progress during the day.

Minus
I am Libra rising with VE (diurnal AS/natal 2nd) squaring PL (diurnal 4th/natal 5th) but also approaching a trine to the diurnal 5th.
UR ruling the diurnal 5th squaring my natal ME ruler of my natal AS and 2nd House in MC

Plus
ME ruler of my natal 2nd House in natal AS sextile the cusp of the diurnal 2nd House.
SA in diurnal 2nd trine diurnal MC (did we say patience here!)
The MO is in my natal 8th soon to move to the 9th House to trine my natal PL (ruler of diurnal 2nd) but later that day.

I went to the casino and won steadily small amounts enough to make small gains... but it was nerve-wracking. (UR square ME)
SA in the 2nd House is not in a position of denial. After all, it makes a trine to the MC
Finally, when the MO from Aries reached the trine to natal PL in Leo (ruling diurnal 2nd and crossing an Angle at the same time that the MO started to rise), I won 3 jackpots in a short-time.
And quit, exhausted!
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The chart blows hot and cold energy. Cold by the hard aspects, hot by the soft aspects to diurnal house cusps.

And here is my list of what to expect looking at a diurnal:
1) No aspects - Not much is going on. People say that the machines are cold. Stay home! You loose
2) Hard aspects - Struggle, win and loose. You are lucky if you break even. It all depends on your own chart. You win and loose
3) Soft aspects - The easiest. It comes to you. You win
I had a case where a woman offered me her seat... and I won a jackpot. People believe that the machines decide whether you get lucky or not. Heaven decide. And the same woman still sitting at my place, I am not sure she would have won.
Here is another story. Once I sat next to a woman who won 3 jackpots in a row. I asked her kindly if she could choose some numbers on my screen. She did and... I won? Yes and No, she is the one who offered me her luck. The energy of a winner can drive and spread itself beyond the person.
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25 wins - 3 jackpots

Diurnal Libra rising this month and transiting VE sextile JU in the diurnal 8th and ruling diurnal 5th
Natal VE in Leo in trine to Fortuna in Sag and also ruling the diurnal 8th conjunct natal MC and the diurnal AS is right in the midpoint.
The MO in the diurnal 2nd sextile SU in diurnal 11th/natal 2nd and ruling diurnal 10th

There is a T-Square involving ME, PL and UR cadent but none ruling my significators.
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9 wins - 1 jackpot

This diurnal extended on 2 consecutive days as the MC was approaching JU in trine to my natal SU
JU is also ruling the diurnal 2nd House/natal 8th
PL conjunct the diurnal AS in my natal 5th
NE in the diurnal 2nd House is trine my natal JU-ME conjunct FOR
The MO will also conjunct FOR (natal JU-ME) and much later conjunct natal SU trine JU.
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There is some hard work involved as VE-SU are making an opposition to my natal JU-ME
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15 wins - 4 jackpots

Some thoughts
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There is no single truth on winning with the planets. I have seen many systems used by astrologers and they all have their element of truth, some more sophisticated than others.
Same for how I use the diurnals and midpoints. Each system has its own limit, what we can call 'human error' because we are constantly asked to make a judgment when we approach the stars.
And there are planetary positions I have seen that will never repeat in time (at least in my lifetime!).
What I want to say is that 'winning' will show up in all systems. Tropical, sidereal, heliocentric, any House system you use and even with some aspects I do not consider in my approach. And they are all good if you are serious in your research.

It is my belief that when you engage in a path, the "souls" of other human beings (dead or alive) who have already found the answers will come to you. What you need to do is to start to walk with all your will 'I want to know', not just 'I am interested by', in the shadow at first to find the light and the answers. You will stumble several times but keeping your focus with a pure intent, you will learn and be inspired by other 'souls'.

With the help of an astro friend, I am now searching for my cosmic souls, I have found Antoine de St-Exupéry, author of 'The Little Prince', who died under a Sun-Pluto in Leo conjunction Antiscia my natal MC.
I can relate to his desert crash:
"On 30 December 1935, at 2:45 am, after 19 hours and 44 minutes in the air, Saint-Exupéry, along with his mechanic-navigator André Prévot, crashed in the Libyan desert, during an attempt to break the speed record in a Paris-to-Saigon air race and win a prize of 150,000 francs. The crash site is thought to have been near the Wadi Natrun valley, close to the Nile Delta.

Both Saint-Exupéry and Prévot miraculously survived the crash, only to face rapid dehydration in the intense desert heat. Their maps were primitive and ambiguous, leaving them with no idea of their location. Lost among the sand dunes, their sole supplies consisted of some grapes, two oranges, a madeleine, a pint of coffee in a battered thermos, and a half-pint of white wine in another. They also had with them a small store of medicine: "a hundred grammes of ninety percent alcohol, the same of pure ether, and a small bottle of iodine."

The pair had only one day worth of fluids. They both saw mirages and experienced auditory hallucinations, which were quickly followed by more vivid hallucinations. By the second and third day, they were so dehydrated that they stopped sweating. On the fourth day, a Bedouin on a camel discovered them and administered a native rehydration treatment that saved their lives. The near brush with death would figure prominently in his 1939 memoir, Wind, Sand and Stars, winner of several awards. Saint-Exupéry's classic novella The Little Prince, which begins with a pilot being stranded in the desert, is, in part, a reference to this experience." (Wikipedia).

After all, we all need to find the inspiration somewhere to keep going.

This one is as perfect as it gets, an offering from the sky.
Pisces rising with transiting JU my ruler in the diurnal 8th and natal JU conjunct natal ME ruler of my 2nd House. The diurnal AS is in perfect trine with my natal ME... on the cusp of the diurnal 5th.
And the MO joins the wagon from the diurnal 8th later when it will form a Grand Trine with diurnal AS and natal ME.
It shows how an aspect becomes important, not just like any other trine from the MO to ME.
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First round: MO trine natal JU
I started to play when the MO was on the cusp of the 4th and was 42' orb trine to natal JU cj natal ME.
But I only won a small amount. As it seems, the orb is too wide to Natal JU but providing some amunitions.
Another small amount when transiting JU crossed the 4th House.
And another one when natal JU was conjunct the cusp of the 11th House but at that time the MO was 10' past the trine.
And both transiting MO and JU have fallen in the 3rd House.

Second round: MO trine natal ME (The diurnal points to this planet)
When natal ME becomes Angular
- Half-jackpot Transiting MO cusp of the 3rd Orb 38'
- Jackpot Transiting JU cusp of the 3rd Orb 20'
- Jackpot Transiting MO from the 2nd House Orb Exact
- Another Jackpot
The last 2, Fortuna Angular in Cap sitting in the midpoint MO/diurnal AS in sextile to both.
FOR is like a house cusp - it activates whatever it touches.

This example shows how the orb and the angularity are providing the scenario on how much you can expect from an aspect. And if FOR shows up in the picture, this is an extra bonus.

The MO ruling the diurnal 5th will conjunct transiting VE, ruling the diurnal 2nd House/natal MC which in turn sextile SA in and ruling diurnal MC/natal 5th.
And later the MO trine Kronos conjunct natal JU ruler of my natal 8th.
This one, I am just acknowledging as I do not have enough data on it. It is still in the evaluation grinder.
JU in the diurnal 8th is trine natal UR in diurnal 5th (aspects between these 2 always bring surprises! Worth looking at when happening)
Minus
MA diurnal AS ruler square NE ruling the 12th in the 12th.
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SA culminating close to the start of my diurnal = almost a thousand K
Biggest win when Kronos/natal JU was at MC in the midpoint A/M = UR/PF = ME/JU = SU/JU
Just acknowledging!
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6 wins - 3 jackpots
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When looking at diurnals, you have 3 levels
1) Natal to Natal
2) Transit to Natal
3) Transit to Transit
At the beginning, it is best to look at the transiting aspects to natal and transit within 1 degree during the day (and the closer the better). You can then concentrate on what the planets rule in natal/diurnal.

The diurnal AS is conjunct natal UR ruling the diurnal 8th.
ME ruling natal AS/2 in trine to SA ruling the diurnal 8th in natal 5th
Natal SU ruling diurnal 2nd House trine JU in diurnal 5th
The MO ruling diurnal AS will contact the SU ruling diurnal 2nd but on the following morning. Dismissed as too early.
But the trine from JU to natal SU extended on 2 days

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18 Wins - 2 jackpot

Here is one of the timing technique I use and it needs to be improved.
***The planets conjunct House cusps***
The orb is 2-3 degrees before and after.
Here I will use transiting ME – SA – JU and natal SU in the last example for May 18th on the 1st day.
I make a listing on a piece of paper before I go using Winning Times by Matrix.
Angular House cusp provide better payoffs

1st round
1) SA cj 6 $$
2) nSU cj 12 $$$
3) ME cj MC $$$
4) JU cj 4 $$$
5) MO/MC = nSU/tJU $$$
I quit for lunch and will come back later.

2nd round -
6) JU/AS = ME Jackpot – JU is rising – ME is setting
7) SA cj 3 – ME cj 7 $$$
8- ME cj 7 – nSU cj 9 $$$
9) SA cj 2 – JU cj 12 $$$
10) ME cj 5 $$$
11) JU cj 11 $$$
The trine from MO to JU is past by 23 minutes. I quit.

Looking at the diurnal AS, you always have 2 options, the transiting and natal ruler, more if you use the double rulership for Scorpio, Aquarius and Pisces.

This diurnal was blowing hot and cold with Leo rising and the SU also ruling the diurnal 2nd House.
MO will conjunct NE in the diurnal 8th in trine to my natal SU in Cancer.
It will also make a square to transiting SU and ME in Gemini.
Both the transiting and natal SU will reach the MC at 2 hours interval.
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Let's look first at the transiting SU in square.
Several midpoints will be activated when reaching the MC - SU/NE, MO/NE, MO/ME which is not a good combination to play around. Better to stay away.

The natal SU looks better because of the trine.
When it reaches the MC, it is accompanied by FOR and the SU is in the transiting midpoints VE/AS-FOR and PL/AS-FOR.
Furthermore, the MO aspect is almost exact.
*** Jackpot ***

Midpoints
Another troublemaker is MA at 7 AQU ruling diurnal 5th in opposition to my diurnal AS.
As I mentioned earlier, the hard aspects do not deny, but it is asking you to be more selective.
I have a spreadsheet for every degree of the zodiac in relationship to my natal chart.
At 7 AQU
MA here/natal SU = natal VE/MA
My ruler the SU involved and natal VE on the cusp of the 2nd House. I can enjoy the moment and I will remember it if someone with MA at 7 Aqu invites me to a party!
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8 wins 1 jackpot

Diurnal Gemini AS sitting in between the NM at 26 Ari and natal VE at 26 Leo on the cusp of the 4th.
Natal VE ruling the intercepted diurnal 5th/natal 10th
Transiting MO ruling the diurnal 2nd
With Gemini on the diurnal AS, the MO ruling Cancer on the diurnal 2nd is carrying the handbag.
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When the NM became almost exact and natal VE culminating I won a big jackpot.
This one, I am still not able to explain at the time it happened. I was working with the exactness of the aspect and VE culminating which provide a small to medium range for winning.
I notice FOR travelling with the AS in Scorpio in trine to my natal JU but it was not my first choice. I was 22 minutes off.
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3 wins - 1 jackpot