The price point for entry and solid cash flow options were the biggest factors for me. 

Bringing my total Rental income to $2800/mo, which would be less once I factor in insurance, taxes, maintenance, and etc.

As a plus, the guy I use is great at customer service, even if he was a little bit higher, I'd stay with him for the lack of hassle factor alone.  

But only under certain conditions and only if you factor macro as well as micro into your decision making process.  

Picking the best option has a lot of factors..

Based on my own experience, a key factor is patience.

In addition to cap x, repairs, management, and vacancy - you may want to factor in rent collection and eviction (time and $$$) and see how you feel after that.

The amount of financing is not a factor in calculating the capital gains tax on the sale of an investment property.  

I don't know cost details yet, and obviously that's a huge factor, but I was just curious if anyone here had given it a shot and how effective it was.

Those improvements are probably already factored into the price.Might make sense for owner-occupied considering you would not have another housing payment and or cash purchase which don't sound like a good fit for you at the moment.Nice job of coming to a decision based on good data instead of "ballparking it."