“In the casino, the cardinal rule is to keep them playing and to keep them coming back. The longer they play, the more they lose, and in the end, we get it all.”
Go back and check up on them after two weeks (the game will notify you), and hope they haven’t decided to run away in the meantime. If they do, just keep at it. Sooner or later they will pay up. Putting someone outside their house before the time is up does not prevent them from running away.
You normally get three courses of action with gamblers:
- Threaten them into paying the debt.
- See what they could offer you instead.
- Forgive the debt (for now) and extend their credit.
If you threaten them, they’ll pay you when you return, or maybe offer you something else if you spare their kneecaps. If you forgive their debt (requires you to have enough money on the crew member speaking to them), you also extend their credit at the gambling house they frequent. Hopefully they’ll sink into debt again, and then you might be able to get a better offer from them next time. Or you can forgive their debt again and extend their credit further. Or, y’know, kneecaps. Up to you.
Threatening and forgiving gambling debts are a prerequisite for a Captain being promoted to Enforcer, but the person doing the forgiving doesn’t have to be a Captain at the time.
Always always always check option 2 first.
Granted, some of the options aren’t always useful, but sometimes you strike gold, specifically:
Business opportunities: Whenever this option is available, take it! If they don’t run away, it gives you a free building in which you can set up a new backroom business. You don’t get to choose the location, but it’s always near where the gambler lives. The size and passive productions (if any) are random too, but hey, can’t complain, it’s a free building. Already have a few spare buildings? Well, have another one! Not like you can afford to buy one, and having an extra place to put stuff is always useful, or build yourself a Small Truck Repair Bay for the increased truck allowance.
If you see buildings offered for sale in the nearby area, it’s probably one of them you’ll get. For free. Sometimes you only get a 750 ft³, sometimes you get lucky with 2500 ft³, and sometimes, if you’re really lucky, 5000 ft³. It’s the luck of the draw.
If there is no building available, you usually don’t get the “Business opportunities” option – and sometimes the gambler runs away (especially when you first start out), but keep with it and soon enough you’ll have more buildings than you’ll know what to do with!
Increased parking space: Second best option. Always useful to have space to park more trucks.
A gambler might also offer you their car (usually a two-door passenger car, not very useful), or a pickup truck (good option), or on the odd occasion a small delivery truck (yesss). They can also offer to introduce you to Corner Hooligans (might get you a Favor with them, and shows them on the map), or improve your relationship with their entire family (limited usefulness – really depends on which/how many relatives they have and where they are). Booze offerings are useful if you don’t already produce enough on your own, or just want some to sell for a quick cash injection.