The property is located 7 minutes from a university so we are hopping to be able to create more units in this desirable area.

However, I feel like the sooner I start, the better, as some of the savings from house hacking (other than creating a rainy day fund for house repairs, of course) can be used to chip away at our student loan burden. 

As for "investor friendly", I learn this saying from a customer of mine many years ago, "Cheap is not quality and Quality is not cheap".I believe in building long term relationships where both parties can make money.

A buddy of mine in tech was telling me how he was playing with the idea of creating a solution to make the closing process even faster and reduce closing fees.

There are reasons loans were created and uses they are intended for.

I am currently trying to wholesale and get some SFR rental properties to create an extra/passive income.

About $75 to create and it is about $300 to continue every year. 

If you do, you may create some taxes, so keep it in mind.

We have our own website and also use booking from HomeAway, VRBO,Trip Adviser and Flip KeyOur high season Guest are all repeat customers and word of mouth so they come through our website.One of our high season guest that we inherited, this was his 11th year on property.

The land trust, it's a good way to avoid probate and hinder a bit the attorney research.Regardless, per my discussion with the insurance underwriter (Allstate), based on the number of properties I have, their current use, and my involvement managing them, my current situationdoes not create a condition where it pushes me to the "business" category and I do not need commercial insurance.