It looks like you've done an awesome job for those seasoned investors.

I have clarification that it is now allowed for the transfer of title into an LLC that you are the majority owner of (borrower(s)) without any seasoning period if you used the second home occupancy loan.

They don't look at employment, income or DTI, and many lenders only require 6 months of seasoning (or less) to use the appraised value.

Just need to talk to a few more seasoned bankers or investors before taking the leap and having your credit pulled more than 2-3 times.  

The area I am targeting is a vacation destination that is rather seasonally resilient (working theory backed by decent to moderate research so far).If I can get past the zoning hurdle specific to mainly "wastewater" - referring to the collection of the toilet, shower, and sinks discharge - I want to purchase 10+ acres that allow me to scale to something quite significant in time. 

Seasoned investors constantly cycle through PMs, contractors and agents as they do more deals.

The seasoning requirements, LTVs, and drivers of the difference in purchase/appraisal values will be effected by the loan product.

And what is the Seasoning Period for VA loans, before you can do the Refi.  ...... 6 months ?

I think Bend is a top place for STR as there is multi-seasonal demand and is a city with a lot of growth.

Winter is slow.So if you picked up a couple of nice, used 4 season trailers, they could do OK IMHO.