Awww Denise you're not whining...never think that...you're here among friends and asking for help, completely normal!!
I'm not expert of course but I think you're feelings of being 'not ok' since moving into your new place probably stems not only for your high expectations of living alone after the transient situations in which you've been having to live in the last 2 years..but also the high stress levels..so it's absolutely normal for you to believe that as soon as you removed yourself from that , then things would revert back to being the Normal you expected it to be, but of course, it won't be..not at first. You're living alon for the first time in a while...you've got new neighbours whom you don't know well and you have to get used to...you're bound to be missing the company of people to talk and listen when you needed...even if you're not missing the negative aspects of some of them ..and even missing some of whom you may have become close with over the last 2 years!!
new area..new home, new neighbours, lack of company...little money...all equates to you feeling lonely I'm sure, and not surprising at all that you're thinking of a possible relationship again, but your confidence has taken a HUGE Kick in the behind of late, and it must seem that you are always going to be searching for the negative in what initially looks like the Pot of Gold in the rainbow..you've been burned so many times with so many things in such a short period, that you're justifiably scared that something you think will turn out well just might not, so instead the your inner self protection will kick in foirst and you'll be searching for the negative in a guy before the positives.
Denise, you know this guy, you've known him a long time...why not go along for just some very casual dating, nothing serious, don't think of it as a possible long term commitment, just go to enjoy each others' company on a fun basis and see what transpires.
It's what I would do in your situation , I wish you luck chica you deserve some!!