Maybe you don't have to be homeless, if it's the freedom aspect you're looking for.
Have you ever thought of living in an RV or camper?
I ask because there are many Facebook group for RVers and the people seem friendly and lead a good and less-costly lifestyle.
With an RV or camper, you could live on your own, but still have the chance to connect with others so you don't backslide and become a recluse.
If you don't have a pet, you could also look into that as well... like a therapy dog. Get you out of yourself (head) and into your body (going for walks)...
Just a thought....