If so, I would recommend to think not as a homeowner, but rather as an investor. 

Currently I have a regular primary homeowner insurance policy on the house as it was our primary home for the past year.

The toothless homeowner taught me so much about humanity and character as well as what people are will to do and say to keep their house. 

Unfortunately very few who seek out these assets take the time to consider their exit and fail to realize they are the most costly assets to exit, let me explain why: Here's how that disposition process to an owner occupant looks: -You will incur turn over expenses associated with vacating the tenant in preparation of the sale -The natural buyer in this price point is the FHA buyer who will normally seek a 5-6% seller assist  -Passing a Section 8 inspection/preparing a home for a low income tenant is very different than the expectations of a home owner,   particularly the FHA buyer who cannot afford to take on any deferred maintenance.

Buy a home with homeowner financing, move out and buy another property but keep the old one as a rental. 

We are having trouble getting the assistance of the entire association for this so we are having the attorneys draft a notice to all the homeowners requiring their participation."

Evolve seems like they charge less but a homeowners have to contract with a local cleaning crew and maintenance.

This means the neighborhoods that have the greatest chance of shifting to home owner neighborhoods.  

Does my homeowner's policy need to be updated to name the LLC as the insured? 

Take AirBnB as an example: no one previously thought that a mass market existed for homeowners to let strangers in their homes, or for strangers to rent their space hotel-style.