But usually it's combined with one other thing ("we don't like the driveway and don't feel like it's a true 2 car garage." 

Then sell, buy a duplex and combine any excess proceeds with your other savings to buy a second rental. 

It's due to a combination of negative growth rates (people moving out) and crime and urban decay, etc. 

Combined rents are $3200/mo, but they should be $8000.

Interesting combination you have here - driver and investor.

My role in this would be to help identify deals, strategy and manage contractors.Thinking about this longer i believe the best strategy may be a combination of 5 flips in the 250 arv range and a couple new construction deals.

There are ways to invest actively or passively, short term or long term, owning property or just controlling it, being a creditor or a debtor and all of those in various combinations.

I'll combine that with the application window when I need a tie breaker.

I have two investment properties, cash on hand to pay one off, and combined equity of about 150k between the two.

HSAs in combination with high-deductible health insurance plans should be available.