Size of dining rooms has shrunk as part of this--we don't have dinners of 12-14 very much.

Most residences are single-family homes under 1500 sqft, with generous lot sizes ranging from 7,000 sqft to 0.5 acres for some properties.Interestingly, despite ample space, vacant lots in this area remain undeveloped with no additional units added.

We always consider gig employment so long as it meets our qualification of 3x the amount of rent and verifiable income for 1 year. 

LLC potentially exposes to me Self-Employment Tax; an S-Corp election requires the payment of a salary; my preference is to avoid either.  

Generally you can weed out many individuals based on income, credit, employment history, previous residences, and overall behavior compared to other candidates. 

We have absolutely no clue where to begin but in speaking with our lender he stated that we would have to find an investor with ground up experience to even begin to be considered for a loan of this size.  

It's so simple, anyone can pull it off, and many of my clients are first time investors employing the exact same strategy.I think you already have it pretty much figured out, but I might suggest incorporating some kind of creative housing in the mix to increase revenue, like STR/MTR or renting by the bedroom.

May also want to maximize square-footage of property in comparison to land size, since land does not contribute to costseg3. costseg/STR: after one year, convert the entire building to AirBnB rentals4.

This defines the size of the deal for you.  

Teak trees are still growing both in Size and value.