I am debating whether to continue to rent them or to sell one or both of them. 

Investors might want to start exploring smaller cities or less-saturated markets poised for population and business growth.

Do you mean just for "cold texting" or even when interacting with clients or responding to real, actual leads?

We get paid the same whether you take a higher rate or buy down, but there are absolutely times when it makes more sense to do it one way or another.

If you want to network or ask specific questions about your local market, go to your local real estate forum and connect with investors from your area: https://www.biggerpockets.com/forums/86-local-real-estate-networking5.

With this type of YOY growth, you can re-invest you equity into upstate or OOS markets (i.e.

Nice to have a mix seeing as it is both a winter and summer destination.Is the place furnished or do you have to do the whole nut?

This could be minor, or major work that we wont know about until that inspector comes out. 

You could form an LLC and have the operating agreement that allows your boss to require you to purchase his membership interest (or allow you to purchase his) in a given time frame.

The more you can systemize the process, the more time you'll have to work on the next deal or venture.