Longer stay rental fits our investment strategy because it's not as short term as Airbnb and not long term renting.

I have found some info on the home and it turns out the owner "lives" there on paper but this property isnt fit to live in in current state (Front door open, broken windows, landscape overgrown, etc.).

Some places are very STR friendly others not so much.Do some research on areas your interested in to see if they are a good fit. 

The 2/5 rule is great and you should absolutely take advantage if it fits better with your investment goals.

My reason for looking into hiring a person with management skills/experience versus handing over to a management company is that the customary method of compensation may not fit very well in my scenario, primarily because my rental rates tend to be well above market averages which will result in a higher dollar amount going to management expenses than would otherwise be the case.

It is one of the reasons for getting my RE license.On the other end, and the initial catalyst for me getting my license is I have a couple of syndicate groups focused on SFH build/reno and lease forming in my network that need a real estate agent and I fit the bill.

There is not a one size fits all solution. 

Reached out to family to help secure downpayment, then negotiated with a local bank to craft a custom "balloon" loan to fit my financing parameters.

That may help you find someone to fit your need best.

I've worked with the former owner on deals in the past and this one fit both of our needs.