When is it enough to give up?

Sometimes it feels so good to be with my boyfriend who I know loves me and other times I feel like I want to run away. I felt this way for a very long time and believe it’s because he makes me very uneasy from a money standpoint but it in particular because he tends to spend more than he should and has an attitude of entitlement. I have even left him a few times briefly for him to try to get his act together telling him we can’t live together until and unless he becomes financially responsible. He brags that he’s really responsible now and in a very in a very good place financially. And I’m really trying to believe him but I just can’t get there. He’s angling to move into my home and even to marry me. Here’s what I do know from my own research. His checking account can be as low as $100 or so after paying all his bills and then goes up during the month as he gets money in from work. At one point he had three credit cards and told me he decreased to two credit cards but I know that he is using another credit card recently again so he’s using all three cards even though I know he is paying the statement balance on the first two cards and assume he will do so when he gets the bill for the third card. He is saving some money but not much each month considering he brings in a gross of $60,000 a year and other than his rent and utilities and his leased car really doesn’t have any extraordinary expenses. I pay for several things that I wouldn’t typically do to help him out and completely try to minimize going to restaurants various trips and the like. So I just don’t feel that I can necessarily trust that he will pay his share of the home expenses that we’ve discussed before. In fact he always make sure to say somethings like well “it doesn’t cost that much really for me to live here if it all” and “look at all the money I’ll be bringing in to help you pay for your expenses“ and “well my friend so-and-so is married to his second wife only pays a few hundred dollars a month to live in their house“ and “my ex sister-in-law never paid for her to live with her boyfriend to live in his house“. This all sounds to me like he’s trying to make me feel guilty about even asking him to share the house expenses even though I know that the examples provided to me are different for various reasons in my situation. I keep on telling him it should be what’s fair to both parties. But I’ve resent these statements. I want to be fair and we do love each other but on the other hand I’m so sick and tired of having to tell him how to manage his money and then seeing him continue to not greatly improve his situation or even seem to care about giving me peace of mind on this topic that we have discussed so so many times.