I have a hard time kicking folks out for any reason, but I let a kindly couple who hoarded food and other stuff and it took 3 weeks to haul everything out and get rid of mice. 

Typically a 6-12 month permit process. Or

Any insight on this process or forming condo association would be helpful.- What would you do if you were in my situation? 

AI machines can extract resources such as minerals and food and distribute them at no cost.

What's his schedule like, can he agree to do rideshare, food deliveries, or a second job on his off days to guarantee rent?  

Yes, unfortunately, the issue you had is a rare one, and one that will happen with any software you use, or any credit card processor you use to collect rent.

we just bought an underpriced piece of land that was unentitled and had high upside in Franklinton in Columbus Ohio. a non profit owned a plot 4x the size an Called us only after our project was announced and asked If we'd buy their site. we gave them 4 different ways they could work with us and their realtor wasn't experienced enough and neither was their director of finance. the bought it to put a food pantry and couldn't because they can't develop. it's a mistake on their part to purchase land like this. their funds should have been used for other reasons.

Was it a long process or was it resolved once you showed the guest list?

You could rent it to a food truck to use 1x a week for $100 a day or $400 a month2.

The Whole Foods/Trader Joes/Starbucks principle works as well.