Suggestions for Me, Please

I've got sort of a problem and I've been trying to find a solution to it. I've had my horse since he was 10 months old. He's 19 now and I've got him at a barn where there's full board and I don't have to worry about him being well taken care of. The woman there lives right down the road from the barn and I call her his second mom. Except, the problem now is she's really his first mom. I'm not into horse stuff anymore and hardly ever get out there. I feel terribly guilty about it and I know he misses me. But, for now, that part of my life has been over with for years. I pay $250 for the board, feed, etc.
And money really isn't the issue now that my truck is paid for. I am just concerned that he's not happy but I can't bear to sell him. There's a lady from church that said she would take him after their place is ready. I have no idea when that will be. But, I think she's going to have land where he and the other horses can run. Where they are now, they hardly get out and then they're just in turnout pastures that aren't big enough to run and have fun. Thanks to anyone who takes the time to read this.

Not sure I understand..lol..the place hes at now, he doesn't have room to run?? Or are you concerned because maybe he doesnt get ridden enough? Perhaps, if you dont want to sell him, you can lease him at the place your at now..That way, someone else could come in and ride him or whatever, but hes still there and you can see him whenever you want but know he's being exersiced..or do you just feel in general its better he has a place to run?? I guess thats totally up to you..if you feel its best for him, then maybe it is..Not sure what you meant really? lol sorry

He doesn't have room to run and the woman that takes care of all the horses mothers him. If I let him go live with my friend, he would be in their back yard all the time and would get more attention. i could visit when I wanted and I would want her to let me know if she ever wanted him gone.

I'm not sure I understand either. You're looking at re-homing Flair or just switching his boarding place?