He must either be a real stunner, or the best man in the sack ever, for you to even consider this!
I cannot see why a woman like you, financially secure, stable, home owner, good job, will even entertain the idea of losing it all to a man who has managed to be 40 years old, with no qualifications, no "proper" job prospects, a string of dead end jobs coupled with unemplolyment, on housing benefit, in arrears with rent, thinks nothing of borrowing money from his long distance girlfriend to pay rent (or other debtors you dont know about?) and removal costs, who cant be bothered to look for work.
Seriously, you need to get some sense knocked into you (in the nicest possible way)
Take my dh. Not a rosy child hood, rather neglected, lived partly with grandparents, partly with his aunt, left home at 16, no qualifications other than secondary, came to London on his own aged 18 from an Eastern European country, worked all hours, kitchen porter, bar staff, hotel staff, went to college in the day time and worked evenings/nights in a pub and 6 am breakfast shifts in hotels, weekends doing silver service waitering at functions, basically working his socks off. Then he met me. Overseas student with wealthy parents, living in a warehouse (cos it was fun). He never asked to borrow money. He never expected me to pay for anything. He wanted to treat me instead. (He never asked about money, or how I was funding my degree or anything). I moved in with him, and we split his rent 50/50 ( a room in a flat share) and went 50 / 50 on bills. Fast forward and he managed to work himself up in IT, and then started his own IT company before the age of 30.
Stop listening to his excuses as to why he has shit jobs and no earning potential. If he has not managed to get qualifications, or a decent job by the age of 40, the ship has honestly sailed. It is not going to happen now.
You need to recognize that you are dealing with a no hope sponger, that feels that the world owes him a living, money, lottery wins, etc.
You need to make a conscious decision whether you want to take on the responsibility for a 40 year old grown man (that you dont really know because you have only been long distance dating and seen each other at the weekends with no responsibilities and where life has been about fun and sex) and pay for his keep, and listening to his no hope dreams and agonizing over this and that job opportunity that did not materialize.
What makes you think he will manage to find (or even look for) work in a new town where he has no network, no connections? He is going to spend months just getting to know the place. Then he is going to start hang out with people, so that he can get close to people who could offer him work. Then he needs to develop a social network, and he will start going out (asking for beer money, cap in hand) and you find that not only are you funding his living, his grooming like hairdressers and new clothes to look presentable for job hunting, his upkeep, his nights out and his socializing.
Good Luck Stella, you need it!