I can say that I have learned from my past mistakes and from stories that I often hear.
- you shouldn't ask a girl to quit
- its not a fuck buffet, its a real relationship
- relationship: there will be struggles because the guy AND the girl have some sort of relationship disorder
- monetary and emotional support
- you cannot "save a girl" if she doesn't want to be saved.
- guy's or girl's ego is too inflated, you need to re-evaluate the relationship.
- being okay with each other's past.
at least these are the things that I've picked up.
I do hear success stories, but not often.
I currently have taken a girl off the market, and I can tell you honestly its not from any special attribute that I have. I just invested myself in this relationship over 3 years. I respected the things that I had learned. Over time it evolved it something that suited me. Its just "committed fwb". I think the secret is to not have too many expectations. She still likes to party which is fine, as I don't make it my responsibility to worry. Overtime she realized she had to get her act together, so life taught her she couldn't party hard and get to work on time and be productive. She has a legit job now and its cute to see her struggle with newbie office problems, like "people don't seem to like to talk at work, they're so focused on their jobs!". If it were to become a real relationship, I would have to see how we both mature. I am not seeking it, so I think that is why its working out :/
so to answer OP's question, I would say, do what ultimately makes you happy. I know some guys take pleasure in taking care of someone or having the feeling of being needed. If you feel like the support is too much to bare, then don't waste each other's time. Everyone grows a little bit after a "breakup".
good luck