Hi Alan,Quickbooks Pro self hosted.I found it to be a pain to self setup correctly despite what they claim, but once it's done, it's done.Best to have a CPA set it up (in my opinion), and your CPA might use a different product for taxes, so the tax lines may not need to be set up.I don't see the benefit of paying a monthly fee for them to host it either.If you are online with it, what does your CPA say the benefit of online renting vs ownership is?

Since then I am nothing more than a pain in the butt to both companies who have both responded to me by effectively telling me that I am welcome to walk away — if that’s what I want.

Now before you say, "...but it's $500/month", I will tell you it isn't.Based on the area you described, and the problems you know you will encounter (as in costs, and late/no rent payments), that $500/month ($6k/yr) will disappear real fast...but the headaches won't.You're chasing a shiny object of distraction. 

Moving is a pain but if I can offer to upgrades to the units I feel like tenants are more likely to stay because they can justify customizing to their liking. 

Its a total pain to go this route.

In our area realtors, flippers haver disappeared since industry pays up to 6 figures as a trainee in high tech.

The yard will be a pain and I need to keep that in mind. 

You are experiencing growing pains!

From day one upstairs was a pain.

Utilities are currently metered as a duplex so splitting util. for the 2nd and 3rd unit would be a pain but if we live there its no issue. when we move out is it even legal to split utilities between two units of different size?