I'll add that you must manage yourself for at least a year (all four seasons, etc.) to have a real understanding of what you want done and how much you would value what is offered by STR PM.

Season tickets to UT football? 

Again, if you feel like selling it you'll be in a good position to do so in the upcoming months(Spring-Summer season).

Seems like a good option is STR during peak season and MTR in other times of year.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

@Matt Wan In the Boston area the inventory is so tight I'm not even sure there's "deals" in the off season.

I could see fully comping 1-2 nights at low season rates, particularly if one doesn't have a lot of reviews yet, but would you, as an established host with tons of reviews, comp a full week or more of a prime season stay? 

Aim high, and have a great holiday season, brother!

If you need me delete my posts I have no problem I am not trying to give you a bad review.I was offering my opinion based on knowing you are "Not a lender" so for me seasoning and being familiar with guide lines is crucial in offering an investor the right guidance and direction for financing.

Although you are a new investor, you actually have more and better options than seasoned investors.Id they need a second parking spot , rent that to them also.