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.

I got my license to be able to be on the inside track of deals and be shoulder to shoulder with others who were taking the same language.

Another thing to look at is if the area you are looking to invest has shoulder seasons that are slower than the main season.

Ask around, this is why you need to be in a local REIA(s).By rubbing shoulders with locals, hearing success stories, educating yourself you will learn new techniques and find folks doing them in your area.