@Douglas J AndrewsHi Douglas, if you are intent on this property your best bet is to get it under contract with contingencies.A key element in making your purchase offer is doing a critical path analysis to determine the steps, time, players and capital needed to pull the deal off.To save yourself time and aggravation, make your first pass offer the the form of a term sheet.

My coworker already retired down there and the guy is basically just texting me the current temp, pictures of the beach or of him fishing...

This sent me for an emotional loop since it looks like there may be some work that was unaccounted for in my initial analysis.

BiggerPockets has always taught me (podcasts, webinars, etc) that I need to bake these into the cake, but if I'm not the one paying them, why would I factor them into my analysis?

This could be harder depending on the area, of course.Perhaps try doing some version of STR with a purchased investment to get your feet wet, and you should at least have a few exit strategies, assuming you are doing enough analysis on the front end.

You dont include the mortgage as an expense.. only on a cash flow analysis..But I can understand why you included 

I regularly receive text, emails and paper mail, even people knocking on my door from my "utility company" and it's a dead ringer for their letterhead sometimes even, but fake nonetheless.And to be clear is it for sewer lateral (waste line) replacement or the incoming service line of clean water to your rental?

The other factors that play in the analysis are CapEx, property management, mortgage, etc. 

Thanks for providing this data and analysis @Robert Ellis.

I have found 11 houses I am interested in, 4/11 cashflowed. 2/4 have become contingent since i did the analysis.