And far less painful than losing money from investing with the wrong people in the wrong deal. 

This tenant sounds like a pain.

Right now you are likely going to run into significant road blocks for ground up construction and STR.

Overall, I think it is really risky as for something that big, it can bring an enormous amount of emotional pain.

Inflation is real and we will have to endure some major pain to bring it down and the housing market is a lagging market indicator as to how the economy is trending.  

Find the ARV of a particular type of home in a particular neighborhood/block/zip code (whatever makes sense for your area) and create an auto email so you get an alert when something is listed at 60% of that ARV.

Bus routes are available within a block.

If done right I believe the home could sell for 350k+ do to the value of the smaller homes on the same block and the neighborhood its in.

Do all the houses on the block have a garage to park a car or all have bootleg units?

If you sold every property anytime you came into a road block you would be selling constantly.Time of year is bad to rent properties, but the fact that you can't get it rented for 3 months now seems excessive.