Partially by circumstance, albeit those that I created, I will confidently say that I am the amongst the very few local Real Estate Professionals that are as intimately familiar with the rules, regulations and requirements to reliably invest in a permittable vacation rental property ANYWHERE on the Oregon AND California Coast's. 

And fellow local investors at a local REIA are always happy to help if you need advice. 

Also, by having to do this VRBO no longer remits my local taxes.

We are on the Eastern shore of Maryland as well :) We run the local REI (Delmarva REI) and have meetups once a month in Salisbury MD.

They do require patience because they are similar to construction where they can take 60-90 days on average to close.You cannot do the work you need an approved GC or builder and typically required to get (3) estimates from (3) local licensed GC/Builders.  

I am also needing to get my loan team dialed in...So, do you also have recommendations on national banks (obviously I'll check banks local to the deals I find), but would like to start with national banks who specialize in this space.

You might try to track down some local lenders who are experts in condo lending to see if they would finance them. 

I'd highly encourage you to come to our next local meetup to networking and learn from others that are investing locally.

Got them through a local community bank in Los Angeles, where I and my businesses are located.30 year terms, 30 year amortization. 

There is probably no regular trash pick up or it is by a local guy with a truck3.)