Okay as I keep chugging along, some more comments:
As others have discussed extensively, the money problem stems from the cost of items being prohibitive. In essence, at the start you have some money but no gear. So you need to buy things, but they're very expensive. Later on as you scavenge items, you can now barter them and your money problems disappear, since you are able to sell them at a high price. I suggest either reducing the price of starting gear, ammo and basic area of effect items, or simply raising the cash amount one starts with.
Next, the issue of conversations. There seems to be really only 2 outcomes (at most) every time: either you manage a skill check of some sort and something happens, or you don't (or don't do it) and something else happens. You could have 3 or 4 conversation choices and pathways, but in the end it's pretty much binary.
Which brings me to the next issue: skill checks. If one is going to have to check skill X in a conversation, and that succeeds, don't follow through with another conversation where skill Y is required or the outcome is significantly worse than failing skill check X. Spoilers follow: you get down a trapdoor, find 2 raiders and an old guy. If you succeed a persuation skill check, you're taken to the boss with 5 others around. If you fail an intimidation skill check, you fight. So if you're good at P and not I, you're unfortunately much better off NOT taking the first P skill check and actually have a fighting chance.
Finally, it looks like for at least the first 4-5 quests of the game, you could be very unlucky in your skill allocations and have an exceedingly tough time getting through. I'm going to keep at it and see if it's actually doable, but right now it's hard as hell for my char inside the 3rd floor of the place that has the vault.