Im a former Marine and long time business owner but new to real estate investing.

You can learn a lot from someone who's spent a lot of time on the property, and it doesn't cost you anything as long as you're polite and respectful.Lastly, you'll want to be ready for the tenants to ask YOU some questions as the buyer or agent. 

But the 2 of 5 rule for excluding up to $500,000 in taxable gains might (we don't know how long you have owned it.)We also don't know your equity position in the property, or how much you are thinking to taking out of it.  

Short term rentals are more challenging in Truckee, as there is a limited number of permits and a currently a waiting list.  

so it needs to be for something short term. 

I will say to forget your idea that you're going to build 10M in real estate just like that - it's a long term game and you have to be okay with a 10-year plan.

In terms of legal perspectives: I found several AriBnb in the areas that I'm interested.

You can also usually get a conventional loan with more favorable terms if you are living in the unit for at least a year. 

Prepayment penalties- usually 1-5 year terms.

How long have you been self managing?