Many distributors also offer financing and can give you an idea of what monthly loan payment you’d be looking at.

I would look at other people's STR photos for ideas or consult a designer.We bought stuff from Lazyboy and they had a designer on staff to help us pick out stuff.

Have both homes completed and sold in less than a year.. and then are taking a much needed break from construction:)Any advice or ideas would so appreaciated!

I would encourage you to speak with property management professionals and a property management attorney to get an idea of what procedures you should have.

Eskiel,This is more off topic for apartments.

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.