OTA business doesn't exist without the hosts and screwing hosts will be the last thing they would do.

After buying the property, I also still have $12k in stocks that I plan to use as a last resort.

I think by waiting to last minute to put things together you miss items and year end tax planning becomes problematic.

The median price in Detroit is up over 2x in the last 5 years.

Lastly is your listing details; they read with all the story telling and excitement of a furnace repair manual. 

I have waived our no pet policy twice in the last few days for guests impacted by fires.  

As those prices fluctuate, there is a builders somewhere putting his feet up waiting to see a market turn more active because the last thing he wants to do is start paying crews to build houses, that could drop in value while he's halfway through the build process and losing equity halfway into the project.

Last thing to look at (and right out of the pages of our client's own experiences) might be starting a transition of wealth in the form of using 1031 strategically to purchase property that your heirs live in until you pass and they inherit. 

Perhaps your #6 of repurposing commercial in to multiple small residential units is the best idea I can see in SA as it has had way too many Single Family rental homes added the last few years. 

I've used to it myself to analyze all of the 35 units I bought over the last few years and personally talked to 100's of other investors who've analyzed and closed on great deals using it.I'd love for you to actually try it and would be happy to receive and incorporate any feedback you have into future releases.