So dad is in jail and the guy is dead.

Most rust belt cities are similar, older housing stock, lower prices, higher risk.  

Housing stock is much older.

You are speculating that it will happen when you need it.Would you buy a stock that requires you pay it $800 per month, hoping it appreciates over time?

I was looking for a platform where I can list the investments for sale but I can only find sites that allow you to sell stock options in private companies but I can't find any that allow you to sell share in syndications (LLCs).

We are still in a very tight, low inventory market- but appreciation has never been higher- it's a great place for a wealth-building investment portfolio- it sure beats the highs and lows of the stock market! 

., stocks or mutual funds) that are operating at a loss, if you liquidate those investments to take a loss, you can use those losses to offset your capital gains.

It's very difficult to simply build affordable housing, but perhaps older housing stock can become more affordable as new housing is introduced.

If your dead set on STR, then do it SMART.

Then the housing stock will degrate, banks will suffer and a circle of misery all around.