Embrace these and internalize the learning.  

The 5-year term without an option to extend would make me nervous. 5 years is both too far into the future to know what external or internal factors might look like, and too soon to be able to react in the event of something negative. 

There may be a time when I want to consider full-time employment, our own internal property mgt for others property which we do not own, group purchase agreements with investors, a "volume discount" from his group for high volume PM, or just even try to understand what others are doing in order to ensure we stay competitive and continue to grow.

Maybe not an issue in your case, but my point is being an owner operator can be protection if STR legislation is passed. 

We now also have internal water damage.  

@Ashley Chris I use Jeremy Bottlinger w Somserset CPA's and Advisors, he does not do the bookkeeping but I believe they have internal. 

Then it has to go through the normal county legislative review process.

I'm considering interning for a property manager this summer.

Still in the planning stage, but I will be using my training/experience as a forester, love of the outdoors, and recent intern session at Earthship Biotecture, to find rural property to develop into small home development, including some off-the-grid homes; maybe some Airbnb options, trails, enhanced natural features.

I am reaching out to you because I'm looking for hard lenders that may want to work on an international deal.I live in Panama (Central America) and I'm seeing some great deals here... commercial properties are going for 30 off.