This is important because the discounted property tax is likely the only advantage of keeping it and that is only present if you move in.  

This strategy has worked tremendously for us, but I'm not sure of demand or rates relative to your area.Keep running your numbers, but don't get stuck in analysis paralysis.

Just my opinion.Bethesda’s Clark Building Sells For $30M, 22% Of Its 2019 Price (bisnow.com)West Loop Landmark In Shadow Of Willis Tower Sells For Nearly 90% Discount (bisnow.com)Blackstone’s Defaulted NYC Office Loan for Sale at 50% Discount - Bloomberg

Then, possibly you can outsource some responsibilities to a lead tenant in exchange for discounted rent?

I had a lease option contract with the owner at a discounted purchase price ( $120,000 ).

A pair of physical therapists and a pair of nurses.I wouldn't discount it if the area has the potential for a lot of traveling health care folks.

If it didn’t meet that criteria and also let me buy at 40% discount with only changing a door handle I didn’t want it. 

They then sold the houses individually often owner financing and selling the notes to me at a discount.  

You could offer the other tenant a discount for allowing you to tap into their wifi for this. 

A felony shows a tremendous amount of irresponsibility, especially if it's his second one 20 years later.