Sounds like he doesn't mind assisting financially in hopes of in the end seeing you grow to become financially independant, take it as motivation to get out of the hole you're in and come out THRIVING!
The important thing as stated is communication. Also you are trying. That is also important. My DD makes depending on the year 10X to 15X what her husband does. He refuses to work anything but part time and considers all his pay his personal mad money. She gets stuck with every bill. He refused to take an upgrade at his job to full time which would then lead to a promotion and doubleing his hourly pay. She is in upper management of a major firm. She is now trying to find to find a way to rid herself of him without paying alimony. Until then she feels stuck.
The easiest way to make living conditions financially equal is if both partners agree to move into a place that both parties can afford at least half of. For example, if your rental budget is 500 a month, then your boyfriend will have to be willing to move into a place that is 1000 maximum.
Now perhaps your boyfriend may really want that fancy place that costs 2000, and is willing to pay 1500 while only asking 500 of you. That is entirely his desire and your decision to agree to it or not.
Like you said, he knows your situation and is in fact your boyfriend. I think you’ll be fine .
That would be fair, but your forgetting the "what if" part. What if it doesnt work and they split and one gets stuck with the full amount of rent/default on it and eviction.