Even your follow up posts smacks of judgement. (The comment about how he's not using his 401k, for example.)
I think you want to be someone who doesn't care what your partner does or makes but you are not that person. So you pay lip service to it, but you can't actually integrate the concept in to your life because it isn't true to your feelings.
I don't think you necessarily need to break up with him. But I think you need to be far more honest with yourself and with him about your feelings surrounding money, and this is even more true since you plan to marry. Maybe he will get that raise. I suspect that if he does, he is likely reaching the high end of his earning potential. Ever. Sure, he might get lucky, but he has a skill set that is a dime a dozen, from the sounds of it, and has nothing about it (danger, unpleasant conditions, etc.) that makes it worth much on the labor market. So this is your life with him, probably forever. *If* he gets that $5-8k raise, and that is the only raise he sees for the next decade, excepting *maybe* a couple percent a year for inflation, can you *truly* live with that? if so, under what terms? Personally, I'd think I'd be okay with a medium-income earner (which is what he is), but not if he wasn't contributing to rent and transportation expenses, among other things. I'd be okay paying more than 50%, but never, ever 100% when he has the means to contribute. I've seen several friends split things based on % of income. If you make 75% of the household income, you pay 75% of the bills. This seems fair and reasonable, though there are several other fair and reasonable ways to divide things as well. Generally, "I pay all of X, Y, and Z and you pay none, even though you have a reasonable income" isn't one of them and few people are going to live that way long term and not feel resentment (for the higher earner/payer) or shame and excessive obligation and perhaps resentment at not getting as much of a say (for the low earner/non-payer). And based on your posts, it seems like you are feeling the things associated with the latter, but you are trying to tell yourself you are okay with it, rather than dealing with it and having hard conversations in which you guys might have some very difficult and awkward disagreements.
You aren't doing yourself, him, or your relationship any favors but not being more candid and by not acknowledging that you clearly *do* have some negative feelings about the current set up. It does seem a bit off to me that as a student, you paid your way, but as a lower (than you) income earner, he is not. You aren't a greedy bitch for not being okay with that. It does seem inequitable and unreasonable. If that's what you feel, that's fine and normal and reasonable. But that situation is that way because you've let it be. So no longer let it be.
In your shoes, I think I'd tell him that in 3 months, he needs to have transportation, and that once his transportation is sorted out, you really need him to start contributing to the mortgage, and that you propose (but are willing to negotiate or try a different approach is he has other suggestions) a % of his income proportion to the % of his income that makes up your total household income.
Also, it sounds like you really need to hash out things like shared expenses. (What about when the a/c dies or you need a new roof?) And especially retirement. I don't think this relationship is fatally flawed by any means, but if you don't address your clear resentments head on, you may well be dealing it a fatal blow. Similarly, if he isn't willing to step up and start using is sufficient income to actually contribute to the things in life he uses, he may be killing the relationship, but if that is the case, the sooner you know the better.
Good luck. Brutal assessment and the resulting conversations can be painful and tough, but it's what is necessary.