You love your boyfriend and vice versa and you know he is very much in love with you (more than you could even expect) but you're always feeling very nervous about his money issue since you have a lot more than him (he earns just enough to pay his rent and other bills and has a small modest savings) and you've also been generous (while he has been generous overall, you help him out sometimes like pay for airfare with points or otherwise on trips he was supposed to be paying in full on his own b/c it is to visit family, etc. with you). He mentioned recently occasion he comes up short in terms of his bank account when you paid for several gifts for his family and friends (the amount was not much but that's not the whole point).
He hasn't been great with money in the past but has learned how to budget better.
He's offered to pay rent to you if he moves in but here's the catch: He pays you less than his normal rent; takes the difference and puts the extra in a savings account for "us" to spend on trips and other things we may need for the house.
He doesn't have much of a safety net other than the modest savings account above that he adds a few dollars to but says once he moves in he'll be able to save more b/c he is paying you several hundred less than his rent. BTW, the amount he's offered is only about 20% of the household expenses.
While you really love him, the "situation" causes great stress and you don't see the relationship growing if you both live separate and apart.
Do you break it off and then really regret it? You have taken some breaks in the past and while at first it is a relief not to worry about this type of thing, you really missed each other and got back together.
Both of you are in your 60s; he plans on working indefinitely and you would like to retire in 5 years.