It will be sold "As-Is" "Where-Is" so the due diligence is on the shoulders of the buyers.

I am not trying to be above the question, but it's true that all financial decisions rest on your own shoulders.

If there was a specific tool that worked head and shoulders above the rest, everyone would do it.

You seem to have a great head on your shoulders.  

On the seasonality issue, while anyone can book the high season, effective marketing strategy and variable pricing will be able to book the shoulder seasons effectively.

If you have a shoulder high window its easier to get away with painting it as long as water doesn't sit on the window sill.  

The benefits to seller are: the headache of that house is off their shoulders and they made more money. 

I then plan to invest that capital into building a marketing machine that brings in more business and thus more capital for other strategies such as fix-and-flipping and buy-and-holding without me having to bear all of the work on my own shoulders (automation and possibly bringing on a small team).

Not paying a state income tax seems to pale in comparison to homeowners shouldering the tax burden.In reality high property taxes does not mean anything.

Sometimes a person with a chip on their shoulder want to vent.