What are my landing options?

I would say most people who enter the workforce and are lucky enough to be offered some type of retirement package (401K or pension) have no idea how to choose from the many options they are given.

I would also research closing cost and down payment assistance options, the more equity in the house you want to purchase, the more likely the bank is to approve you.

Agreed on the in-kind not being the best way to fly, but it was necessary for at least a couple of years - RMD's exceeded rental income and selling wasn't an option. 

Owners mistakenly ASSUME all PMCs offer the exact SAME SERVICES and PERFORM those services EXACTLY THE SAME WAY, so price is the only differentiator.So, the first question they usually ask a PMC is about fees - instead of asking about services and HOW those services are executed.EXAMPLE: PMC states they will handle tenant screening – what does that specifically mean?

I feel like that's a good option with okish cash-flow.

I offer this exact deal in my markets. 

I specifically need really user friendly accounting features (including ability to sync with quickbooks and print checks directly from the site/software), customizable online application, and online rent-pay as an option (hopefully with free or very cheap ACH). 

This is a core deal, which certainly offers some risk mitigation, as they allude to.  

4 units are great because they give you the option to rent some units out while you're working on fixing the other ones up and there is a lot of rental demand in Cleveland and surrounding neighborhoods right now, so it's a great time to get in the market!