what factors should I be looking at when making this decision.  

Definitely speak to your accountant.2.When you go to refinance, the lender will look at several factors - the value of the property, use of property etc.

It could certainly be a concern - but depends on a lot of factors - are you looking multi or SFR? 

There are markets that have built in "gotchas" like the rising cost of insurance in coastal FL, regulations in much of the west coast states and property taxes in Texas; however, the deal itself is the most critical factor.

Oil prices remain a huge X factor, and housing prices (at least with respect to rents) are being held back by the most supply EVER being built and coming online here in 2024.

That is something that is growing due to the limitations of STR.MTR is something that will help you but you will have to be a bit flexible in the times that you are planning to come in.Management is cheaper than STR, but you have to consider other factors such as close to places where those MTR are in need.

That’s the very simplified version but raising capital is always your biggest limiting factor so the more investors you can connect with the better. 

I take full responsibility for ever having trusted a person so blindly.

You can put it all in that until you figure out what to do.One thing you didn't factor in your post is taxes.

Most times landlords don't have data or cannot adequately factor in vacancy time or turnover rate.