Looking at this property as a long term rental strategy.

So, your focus may need to pivot from high rental cash flow to little to no cash flow as a rental with an appreciation upside.I would recommend taking your $150K to $200K and securing a solid equity position in something that will cover its expenses and maybe provide a small cash flow, but then is poised to appreciate nicely over the course of the next several years. 

I would only place it on DeFi if you're fully aware of the risks, or as a smaller fraction of the CeFi.

- properties going at a time as a sort of hedge against 1 contractor holding me back on 1 property rehab.

If you can involve the local fire department to help with defensible space as a start. 

The property is cash flowing $10-15k every month and has been an absolute juggernaut as a short term rental.

Here’s our OPINION for the Metro Detroit market (use as a template for your target area!)

I wish I would have kept this as a rental.

I'm curious about this particular scenario because I'm imagining it as a way where all 3 parties (in this case) can get something out of the deal.

Say they sold the properties over 3 year period and could not sell the rentals together as a portfolio.Could they put the money from each sale into a DST then use the total to buy a expensive rental property?