I am sure something will come up as I am still relatively new to the STR hosting.

The more time you spend talking about other options and try to build up the negatives, the less time you are spending on what you fell are the positives of your own idea.If you believe that you are onto a great idea using L2P option contracts and forming partnerships where someone else provides 100% of the money while you provide 100% of the real estate-related functions, then start it up and make it work.  

For $10K and a lower rate I'd be willing to consider delaying...but only if I knew that lender two was solid on closing in a relatively short timeframe.

The other ~25K is related to tenant issues.2.

BUT, I am sick living in construction and would like to move to a new home and then finish fliping and sell or hold the two homes asap.

Whether we are related to the landlord from our previous rental, and if so, to specify the relationship.3.

I don't see how they relate to wanting to educate myself or asking for reading recommendations. 

I currently live in Tennessee and I have a possible opportunity to in move to the state of New York for a two-year work-related contract come the summertime.

What makes you an expert that the unit is in a great location & condition and the market is hot, relative to the property manager?

I'd insist that he find a non-related handyman or change PM's.I agree a huge red flag to me is 24 hours of labor.