That's a tough one. It is great that he came and discussed with you and seems OK with you leading the decision.
Personally, financial stress is huge. Perhaps having extra cash flow will help your R in the sense that you can focus on non-$$ things for awhile.
I'm also of the belief that a WS can't be controlled, i.e. if he wants to cheat, he'll do it anywhere. I'm not about to control my WH's environment in an attempt to prevent cheating because, well, I don't think it is about the environment and, frankly, I want him NOT to cheat because that's not who he is anymore...not because I blocked him from all temptation.
Having said all of that, your D-Day looks recent? And triggers are triggers - so if the bar environment will trigger you that badly, it may not be worth it.
Why not take the job and give it a try with an agreement to check-in frequently about it. Would he be willing to quit the job a few months down the road if it isn't working for you? If so, then I'd say you've got nothing to lose because the decision isn't permanent.