We have a third property a few bocks away that is a 3 Bed/2 bath.

Quit expecting the tenant to 'perform' for you. 

If this fails, then perform a land trust strategy.

It reminds me of the Charles Schwab study - their best performing retail investment accounts were from dead people that never closed out the account.

The real estate investing industry uses "Classes" to rank property performance risk, but there's NO agreed upon industry model:(Here's what we use for our Metro Detroit market:Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

I’ve tried VRBO and Furnished Finder, but they didn’t perform well in my market.

There are actually THREE kinds of subject to transactions1- subject to existing mortgage without lender approval2- subject to existing mortgage WITH lender approval3- subject to existing mortgage as part of a seller financed wrap around mortgage.with #1 and #3 it’s in everyone’s interest to utilize a third party servicer, who collects and then distributes payments.  

Be sure you are comfortable with the math and know exactly how much you should be getting depending on how the property performs at different levels.  

A third party company that integrates with our system.

While metrics like square footage or price per square foot matter, the number of bedrooms, bathrooms, and overall location are often more critical for attracting tenants.Engaging a property manager early on can save you from costly mistakes and help you invest in properties that perform well in the rental market.