Or if you have done this or anything simular to what I am thinking I would love your input or advice on how I should proceed.

I Review what other properties simular to mine are actually paying and argue that if all these similar properties are paying less then I should be too.I have always got a tax reduction. 

I am currently in the process of starting something simular as well with a business partner of mine. 

Lets say someone wants to sell a home for $1m - Is it possible to buy it for $1 and then have a legal document drafted or simular saying I just owe the owner $1m as a gift so the property doesnt register as $1m purchase for the assessor?

I recall a simular post a few months ago, @Ryan Mullinsorry for the PTSD flashbacks, I don't you were at fault.

Mechanics use a simular method and it’s accepted as industry standard, some contractors have resentment towards that fact, some just don’t want to deal with it, and they feel their price is their price. 

@Lamont ChenGot it that was very helpful ,another question would be what if that area didn't have any comparable property sold with in a decent time frame, also what if there were no simular properties to relate too ,such as lot size or square footage

We had some simular experiences- lifelong tenants who didnt know how to take care of things or how to save to get a down payment. 

My demographics are simular to yours for the most part.

I would manually look up simular properties to what you might buy and check their occupancy and nightly rates.Cleaning fees are paid by the guests and are a pass through.Read through this forum for plenty of tips to getting started.