I am thinking about buying a vacation rental property there primarily for short term rental but will use is occasionally in shoulder seasons.

Based on their experience or what they read on social media, some people have a chip on their shoulder and believe that relationships with their landlord are supposed to be contentious power struggles against "The Man." 

I was willing to manage the property for free with him as being an occasional backup while shouldering most of the financial risks.

Management companies typically earn about 10% of your monthly rental income so shouldering the management and maintenance will increase your profit margins.Let me know if you want to chat further or start looking for good opportunities.

I would imagine seasonality would be a factor too where the yurts or whatever type of camping set up you have may not provide shoulder season comfort  whereas a tiny home... may? 

Your question varies very much as I know the utilities are on per LF basis from their last point of contact (POC), if your neighbor that has electricity 20,000 ft away, it will greatly vary if they were 300' away, just like construction, they will pass the cost to you, have you shoulder part of their overhead and etc, that's just the basic rule, you're simply paying them to work for you, just like hiring a sub that you don't have a choice but say yes.

It sounds like you have a great head on your shoulders and you know what you want.

That doesn't mean you have to be looking over their shoulder at everything, but we do live in a digital age, use it to your advantage.

I figured that way I have some stability of income during the winter months and I could potentially use the top unit in the shoulder season when it is not booked (although I am sure I will regret it when tax season comes around).

FYI, I'm in Bend, Oregon, not Portland, which has a thinner tenant pool, especially in the shoulder seasons.