To your question:  you are going to want some reserves on hand - if you don't have the funds for the down payment, then you don't have the reserves...I would not take that property on. 

*  What requirements and contingencies (i.e. umbrella and earthquake insurance policies; ex to forfeit some or all of her share of equity to make me whole, etc.) would you include for protection against possible forms of loss (i.e. lawsuits, natural disasters, mortgage default, property neglect/deterioration, etc.?

Purchasing the home is going to put a huge dent in the reserved.  

So that when the inevitable happens, you will have a prudent reserve set aside to cover those costs without impacting your cash flow.Lastly, I'd advise setting a further 10% aside for a property manager. 

Then of course there are direct bookings and VRBO/BDC reservations that are processed through Stripe...

There were a few things assumed on this, which make me question how good the numbers look - assumptions being that I could negotiate to a purchase price of $90k and that each unit would get $700/mo for a 1br/1ba.That said, here are the questions that I have (I understand that some of this will come more naturally with better understanding of the local market, but as I build that knowledge, I'd love to see what people here have to say):- Are these assumptions too aggressive?

If you are in a situation where you are holding the apartment until the tenant has the rest of the funds, we use a 'reservation fee' and have the potential tenant sign a reservation fee form.

I've poked around the marketplace but I'd really appreciate a reference to an eastern Kentucky licensed realtor who is internet savy and has the experience to list 277 acres w/a house and barn w/heated conc flr about 10 min from Natural Bridge State Resort Park, Wolfe County, KY.

Property has good reserve and ability to carry itself.

@Bryan Richard Population of the town, loan size, occupancy must be 80%+, quality of the mobile home park and debt service, a credit score above 650+ and have 6 months of reserves is critical.