Is my boyfriend broke but says he is financially settled for us to live together

After many years of my bf struggling to get his finances in order and with my non financial support to help him budget and financial gift from a family member, he tells me he is really happy with his finances so we can plan to live together. In the past, I told him I wouldn't live with him unless he was financially responsible, like me. Well here are the facts... He has paid off all but about $1,100 of current balances for cards, with 1 payment due 2/1 and another shortly thereafter. Of course, this will go up over the next few weeks with purchases of food and gas. He is current on his rent and other obligations. He only has about $300 left in his checking account after paying bills but will get 2 paychecks this month and a social security check so he'll have a lot more later in the month but will have to pay the 1st of the month bills again, including rent. It seems that he basically "breaks even" each month but no better than that. He has a small savings account I helped him set up (with his own $) that he contributes a small amount to each month. He still has some of the cash gift left (about $20K). He has no other assets or retirement accounts at all. He is retirement age. Now he says we are "entitled" to take a vacation somewhere warm for a weekend and he is paying for it all! Really? I usually pay 1/2...why all of a sudden and in any event, he is broke in my eyes and if so, what is he doing taking a vacation at all??? Is he trying to mislead me that he has it so together that we can still have a nice lifestyle so I don't leave him? Am I crazy and is he is a hopeless case since he still wants to live with me?

Hmmm I sure I just answered a similar problem to this!