This is quite the busy chart. First, let's pin down the significators. I am using techniques described by Masha'Allah from his work On Reception as well as from William Lilly's Christian Astrology. They are remarkably similiar.
Both astrologers assign L1 and the Moon to the querent, L7 to the person who borrowed the money, and L8 to the money itself, though as you will see L2 has a part to play too.
Masha'Allah: (I am paraphrasing, not quoting. Yes means the money will be returned.)
1) If L1 or Moon apply to L8 or to a planet in the 8th then yes.
2) If L8 joins a planet in the ASC with reception then yes provided the planet in the ASC has some dignity there. (Note, reception requires an aspect, Masha'Allah would have taken an applying aspect by sign not just orb.)
3) If L1 or Moon joins to a malefic with reception or to a benefic in a strong place then yes.
Lilly: (Again, paraphrasing)
1) If L1 or moon join to L8 then yes.
2)If L1 or L8 join to a planet in the 8th and it is a benefic, then yes. If it is a malefic and there is reception then yes. If no reception then no.
3) If L8 is in the ASC then yes (classic emplacement.)
4) If L8 is in the 2nd and received it's possible.
5) If L7 or L8 are in the 1st or 2nd house with reception from L1, L2 or the Moon then yes. Without reception then no. (keep in mind, reception requires an aspect.)
6) If L1 or Moon join a benefic that has dignity in the ASC or a sign intercepted in the ASC then yes.
7) If L1 or Moon join to a malefic who has dignity in the ASC with reception then yes.
8) If L1 or Moon join to a benefic that is well placed in the 10th or 11th house with or without reception then yes.
As you can see, the two are very close to each other in technique, with Lilly spelling it out a bit more clearly.
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So, querent is Venus, which adds to the chart as Venus also signifies the money lent--they are one in the same, posited in the second house. Clearly the chart is describing the situation. Moon is co-active. The colleague is Mars, in detriment and combust in his turned 6th house. Notice though that Mars is escaping combustion, meaning what ever has been impeding him is resolving. Likely something to do with his turned 4th as that is the house the Sun rules. Mercury is retrograding away from him but will turn direct shortly and I have to wonder what that's all about...at any rate our borrower is going through some things but they are starting to get better. He's not quite out of the woods yet so it's going to take some time.
Meanwhile, if we follow our indications above, and look at the chart to see which aspects happen first, the next thing that's going to happen is that Moon will conjoin Saturn, with reception as Saturn is in domicile in Aquarius. That ticks a box for a resounding yes, since Saturn has dignity by both exaltation and triplicity (day chart) in the ASC and in fact can see the ASC by a trine.
If we follow the Moon's path we could check off more of those boxes but we already have our answer. The caveat is that the next aspect is to Saturn, which notoriously indicates delays, in 2 degrees/units of times. We could be hopeful and say months since they are in an angular house, that would be best case. Worst case, as Aquarius is a fixed sign, is two years.
hth
Tamara