I plan to ideally keep the property as a long-term rental, but I'm aware that by the time I'm ready to rent it out, it's very possible the value of the home will have dropped, since the price of the home is likely inflated somewhat due the current market. 

@Ryan Kinley I like to ask this question "Other than price, what would an ideal transaction look like for you?".

Ideally, we would love to sell the property as it has appreciated more than 125k since we bought it and it is 120 years old, so I am afraid major expenditures could be on the horizon.

Ideally the PITI (mortgage, taxes, insurance) is fully covered by the roommates so that you are only on the hook for expenses. 

Ideally you’d arrange with the friend that he would get all his money back plus interest at closing of the sale as opposed to monthly interest payments.The other option is equity, where he would split profits.

Brewsome seems like an ideal place to have them haha

We'd be looking for a smaller cottage, preferably not too far from a large body of water, ideally sub $200k.  

This behavior is ideal for scammers!

One of the things I have started doing is looking for the types of chain restaurants that my ideal tenant will want to frequent as they will have already done the market research for me.

I would sell the house and not rent it out. 1031 ideally into multi unit(s) that cash flow well and rent a personal residence in the meantime. 1031 is the key here since you are sitting on a massive gain on sale.