It’s an excellent bookkeeping, accounting, and rent collection tool specifically designed for landlords and investors.

Simple, connect with those that " handle it all" YES that simple :) I know many from around the world that do absolutely nothing but close, everything handled for them Good luck 

If you are willing to rent rooms, it is a simple equation and you can live for free, it literally is just finding a house where you can add multiple bedrooms and turn a 4 bedroom to a 7 bedroom or a 5 to a 7 bedroom and you take the smallest room or a trailer and renting out 7 rooms, you can definitely achieve cash flow.

Other than that it was fairly simple and hassle free.

Like should flooring be simple enough?

A big part of guest experience is design and functionality of the home.

I've seen some simple templates circulating the internet and this is nothing alike.

I'm with you on the simple NDAs.

Don't have to be on the deed even to declare it your homestead.It may be splitting hairs, and I may have been unclear in my initial post, but I believe homestead laws are designed in part to protect non-title holding spouses, so if the new wife moves into her husband's house he cannot sell or mortgage without the wife's consent nor can it be forced to be sold to pay involuntary creditors (as opposed to voluntary creditors such as mtg/DOT lenders). 

It's a change but as you mentioned you don't want to down grade the property to a single family, but maintain the 2-family designation.