First, ensuring that each property or group of properties is held in a separate LLC can limit exposure, confining potential liability to the specific entity involved.

They are a great way to meet other local investors and learn about market trends.

As a note investor, we rarely if ever originate loans for owner occupied, we would rather buy on secondary market at a discount. 

It's a great strategy and you're in a great market to be in. 

There's no contest, although some other countries could work as well in specific niches.

Every nightly rental review that has one, is only positive and they usually have 100s of reviews(at least the only ones I can find).I wanted to stand out in my market, while checking the box of "hot tub" since it's a standard amenity now. 

You've got several options depending on the specifics.

He has acquired the land, gotten the permitting, has construction financing lined up but needs ~20% cash equity / home.I know very little about his particular real estate market, and I've never built anything myself. 

Those brands are just great marketing companies, not necessary good windows.

Renting to a group home or adult care facility can be a viable option, but it comes with specific considerations.