I do recognize the GR is an extreme case and hopefully we do not experience anything similar to GR.So their theory does not match my reality as someone who actually had well established STRs at the GR.I suggest you be leery of people who present theories without any experience related to their theory. 

The reason for this mainly of because I can get a bigger loan on the house we have just built, than taking a ground up new construction loan on the rental we are wanting to build next door as well as my experience with ground up loans is zero -  a lot of lenders look at land and don't' give value to it, you need to establish the fair market value of the land through a transaction.

It's a very popular area for weddings, with Bainbridge Island close by, Kiana Lodge (Poulsbo) and Port Gamble.

Additionally, if you got a loan on top of your cash advance (say, you only had enough cash for a down payment) then I imagine you're also paying loan fees twice.This may all be fine and dandy if the numbers work, but is this a viable plan or a total gamble?

If you currently have such self-employment, your business can establish this form of simplified Qualified Employer Plan.  

I’ve established back-up to my systems and standards through a contractor who also manages several properties.

Tutorials  emphasize the need to do due diligence on all the following:--check for taxes and liens against the property--find out which taxes and liens, if any, will remain attached to the property--make sure it is a buildable lot--to do above, you need to establish how the lot is classified for code purposes, and access the lot specifications, minimums the lot must meet for construction to be allowed--you further need to find out what its sewage situation is because 1) municipalities have different lot minimum specification for lots with public sewage and lots with septic; and 2) if the lot will require the construction of a septic tank, you need to take that into account in your decision.

Save the Guru fees, Mentor fees, and invest, instead of gambling with someone else's credit and life. 

I am in a time crunch as I assume I can't list and show the property until I have the legal framework established.

Seek advice from legal and tax professionals to establish the most suitable structure for your US investments.