An older investor should focus on cash flow because time is no longer on their side.

If you get enough experience doing exactly what you did with your first property there are lenders that would no require your purchase to "season".

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

If you’re paying off less than $800/mo on your loan id say sell come April selling season.

Older houses going for $600k isn’t gentrification though.

I would advise to look on here and try to connect with a seasoned investor in your area and maybe they can refer you to one.

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

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? 

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.