Just look around at other local banks and CUs.

We're looking to build something unique/contemporary with of course elements of the local area (mountain town).

Quote from @LeRoi De-Souza: Go to BUILD YOUR TEAM at the top of your screen and you can search for other MEMBERS or LOCAL MEETUPS.

I'd recommend reaching out to a bunch of local lenders to tell them what you're looking for and your situation.

I have been volunteering with local Habitat for Humanity groups to learn how to renovate houses, and currently looking for my first house hack or flip in the southeastern MA area (have been looking at areas such as Barnstable, Plymouth, and Bristol counties). 

I've personally worked with a handful of "investor-friendly" lenders, primarily on DSCR loans in recent years, and each time I've run into significant delays, lack of transparency about the process, have been fed the requirements in a piecemeal fashion (every few days there's a new random request rather than having it all organized from the start), and have even run into lenders who were substantially misinformed about the real estate industry or the laws that govern it on both a local and federal level.I think there should be a better site to encourage accountability by tracking how long it actually takes each lender to close their loans on average, and what unexpected hurdles investors encounter when trying to work with them.I can't seem to find such a site.

Go to BUILD YOUR TEAM at the top of the screen and look for local investors or meetups in your area.

Do you focus on local Florida cities or do you diversify across multiple states?

I'm suggesting the opposite: go to neighborhoods the locals tell you are good to verify that they are good. 

Buy in your local area and learn hands-on how to operate multifamily properties.