The idea of “giving back” by providing the kind of experience you’ve appreciated as a traveler is such a fantastic approach and will definitely resonate with renters, especially healthcare professionals.Single-family homes and cabins sound like a perfect fit for what you’re envisioning.

Perhaps your #6 of repurposing commercial in to multiple small residential units is the best idea I can see in SA as it has had way too many Single Family rental homes added the last few years. 

Would it be a bad idea to buy a single family home built in mid 1930's?

Why would anyone start the purchase of a property, having zero idea if they can actually execute their business plan? 

The umbrella is a good idea as they are usually not too expensive for the amount of coverage.Get a good STR policy.

Love to see so many strong opinions on this topic!

I think a new administration brings new ideas and new people.

I am very new to this idea, so it's possible that one of these options just doesn't make sense.

I just don't like the idea of single member LLC because then what if something God forbids happens to one of us or when we have a family how do we ensure that this is legally theirs?

It's usually a very bad idea to go into business with friends or family.