New Man Blues

[cherryteat]

Hi I am nearly two years divorced. For the past six months I've had an on/off relationship with someone I really like. We have great rapport and sex is brilliant. He's kind, loving, funny but the flip side is that although he has his own business hes a bit of a flake and buries his head in the sand when it comes to debt and other serious stuff. His family are well to do and regulalry bail him out when the shit hits.
When I met him he was renting a huge house that he can't afford, his housemte had left him in the lurch and the agents had out the house on the market. He was living way beyond his means and as I didn't know him that well I presumed he would just find another place and deal with the problem in an adult way.
This didn't happen,he miserably opened his house to potential buyers whilst whinging to me that he was upset having strangers looking around his house. Every now and then he seemed to be pulling his finger out and looking at properties but it was shortlived.
During this time he admitted to a lot of debt, valid reasons, ill health and self employed so lost income, housemate did a runner, left unpaid bills and it appears he never got his act together.
Parents bailed him out once a few months ago then the house was sold so they jumped in again with a deposit and months rent for a new place.
Sale fell through so the urgency lessened so he has used parents money to pay some debts and has eased off looking for a new home despite the fact that his contract ends soon.
Sorry I have gone right off on one detailing his situation...
If you're still reading, I just don't know where to go with this. We have a great connection on many levels but his lifestyle and attitude to money and housing is like that of a twenty something rather than a man in his 40s. He has a real Peter Pan thing going on which in many ways makes him cute and fun to be around but he also exasperate me.
I'm a middle aged single Mum, I feel as though I've invested a fair bit of time in this and I also feel a bit like I have inherited a third child...he would. Do anything for me and swears he's getting his shit together but I see no evidence of it. Am I being too controlling? Should I mind my own business? I would have liked to have just had lots of fun, dates, sex etc but he has confided in me and I find it hard not to take this stuff on and worry about it.
Thanks for perservering with this!