Can I trust that my boyfriend has really changed for us to live together?

My bf and I have been together for several years but not living together. I am certain he is very much in love with me and I love him BUT the one issue keeping us from moving in and moving forward is what I see as a red flag...specifically, his financial judgment (or lack thereof). It also doesn't help he doesn't have much money or assets to his name and I'm very well established after working my a** off all my life and saving. He works but only earns a modest salary and collects social security. To be clear, he appears to keep up with his bills but doesn't have anything much in his checking account after paying those bills - in other words, he "breaks even". Further, he has NO retirement savings but does have some $ put aside equal to the amount he earns in his job for 1 year. I told him I will never live with him solely b/c I am really anxious about the possibility of supporting him at some point and he will be required to pay me rent that is at least equal to the amount he pays now (which is far less than 1/2 of my actual household expenses). He is really trying to keep his expenses down and now says "he's really happy where he is financially". I suppose being able to pay most of your bills makes him in a better place than before when he owed thousands of dollars and was unable to make the payments until a "gift" was given to him by a family member who passed away. The real question is it practical or even possible for someone to change this much to the point where I can rely on it? He has disappointed me many times in the past but I do see some progress. One of my adult kids does not like him or trust him based on his history. That creates a lot of stress between me and my bf - he thinks he should be "recognized and acknowledged" by my adult kid despite the way she feels. does anyone have any advice?

I'm actually in a similar situation but my boyfriend recently went from barely making it to completely unemployed. He hasn't shown much interest in changing things either. My guy went through an extremely rough situation and as his woman I though maybe I can build him back up. After all I may be getting a promotion and making more money. Just moved into my new place and after busting my ass and working 3 jobs 6-7 days a week have managed to put myself in a decent position in the world. With my new found financial security I figuered maybe I can help get him back on his feet but he has thus far seemed perfectly content to sit on his ass, eat up my food, watch my TV, and use my internet while I get up early every morning and take my ass to work. I'm not saying your guy will do the same but thus far my kindness seems to be taken for granted. He's even inviting his family members over and offer them amenities like he pays for the shit. Proceed with caution ion because guys are getting shameless with their mooching.