Well I was young and stupid, and I bought a fucked up house in NOLA for $7000 (I borrowed most of it) off craigslist on impulse. Was gonna purchase it then create a nonprofit co-op with my friends to transfer the property to. Had friends in construction who said they would help with repairs. Had friends who said they'd invest in the repairs, help financially, commit to living there... I guess folks thought I wouldn't actually go through with it, or didn't realize the scope of things. I certainly didn't. I was doing weekly meetups/cleanups where we worked on the house. Everyone just kinda... dipped, stopped coming, avoided me, you know. It turned out to be kind of a scam anyway. The property had tons of liens and shit that didn't come up in the initial title search and all that, shit's so corrupt down there. They started fining me hundreds of dollars a day for not having things fixed up right off the bat. Someone came and filled up the dumpsters I ordered with their own construction trash. I was renovating it by myself for months. The city was impossible to deal with. Couldn't sell it. Literally offered to give it away to cool groups if they agreed to take on the fees, but no takers. Eventually I just got super depressed and got into an abusive relationship, started doing hard drugs and gave up on everything, and just abandoned it and left traveling again. Figured the city would just sell it at auction eventually and I'd owe the govermnent money forever. Didn't think it was even still in my name but a couple months ago someone got a hold of me and offered to buy it for $10k on top of what I owed. A fuckin miracle. So yeah that's also how I have money now.
I ended up moving back into the co-op that inspired me to try to start my own in the first place. Right as I moved in it was nearly shut down do to all sorts of problems, social, financial, blah blah, so got invovled with the board, went to court, dealt with the city, and have been grinding my ass off to get it back to it's former stability for 5 years now. Overall, I've been successful. I've learned a SHITLOAD about actually running a nonprofit, it's pretty much been my singular focus and the only thing I do with my time. I've learned a ton about how they can get fucked up as well. There are a lot of moving parts when dealing with property, people, housing, and bureaucracy around them.
My passive dream plan is to start my own co-op type situation, and has been for about 8 years, so I've put a lot of thought and investment into learning about it through my own experiences and talking to other people and orgs. Also got that OCD so it helps.
I would reeeeeally suggest starting with putting together a solid, invested crew that is willing to work on this over a long period of time. Everything will fall into place from there. I was initially very much in the mindset of "if I build it they will come" myself, but I've seen that create more problems than it is worth in many situations, and have completely changed my view. I'm personally about to head out to travel again in hopes of ultimately finding a solid crew or a spot worth investing in.