I also figured i do a little writeup on your starting options to get stuff fast: (cash in brackets)
items:
O'Shay - 0 stat checks for drugs(1.3k), lockpick(120) and if you rape her gun(390). (i find all of these better as items than as cash though)
money:
1. Jealous Wife - you help in the murder and optionally rape and you can choose to take the car (4.6k) and get the ring (1.5k) as a bonus with 0 stat checks
2. If you reach sex level 7 - sleeping beauty to meet wade then motel girl will allow you to give her to wade, except you actually rent her to some mafiosos paying you 5k for the pleasure and then phoning you next day to tell you they accidentally killed her where you can settle for money for another 5k.
sex/brutal/mind control xp:
little troublemaker - can trade drugs for a harem type of your choice (slave,brothel,harem) with 2 girls to start. This allows you to spend your daily stamina before hunting on stat increases for sex skill and either mind control (brothel,harem) or brutality (slaves). Only upside of harem over brothel is you can turn them into slaves if you have negative disposition and you need hypno and brutal xp.
incubus xp:
1. sister of many - bring a lockpick to rape those you didn't seduce and 4 in mind control to get the mother too. 5-6 impregs
2. unfortunate souls - having brutal 3 will give you the most time in this dungeon though incubus 4 will also give you access - there are 3 rapes and 2 seductions on slaves here (some need lockpick) and the ov:x canister(680) though that will cost you a lot of time. You can also return to the slave in the westernmost part after fucking her and take her along - she shows up in some events and gives you 2.2k cash at the midnight fence. 5 impregs
3. whorehouse - needs ov:x canister or gun to disable impregnation blocker as well as money for the whores - up to 1350 if you use the gun, 1950 if you use ov:x and bang the receptionist but that also deletes any leftover cash. 4-5 impregs
4. woman down on her luck - needs drugs to get you 3 impregs
Edit: A note on Starts - here is a guide on how to get ending 18 which unlocks the excellent brothel owner start (start with 1k money and 5 whores)
1. Jealous Wife - assist in murder, get the car
2. Sell car + ring, buy ov:x ( even got enough spare to buy wapal indulgence if you haven't got it yet )
3. whorehouse - go north and replace canister with ov:x , do a circle fucking all 3 whores without bribing them, then ask receptionist name and offer her all your money to fuck her
4. rest until season end