Why am I selling? Should I be doing something more strategic?

[John D.]

Thanks in advance to any/all feedback.  I presently own a two family rental in the North burbs of Boston.  I have a little over 100k in equity but the market here has been crazy and I was thinking of selling it to buy something I could rent / use in NH vacation/ski country.  I had the epiphany today (I'm not a finance guru) why not take the equity to make this second rental purchase and do a smaller (condo maybe) in ski country and keep my rental.

Part of the proceeds that I make each month from the rental pay my student loan debt and my truck payment so the proceeds from the sale were going to pay them both off and the rest would be re-investment capital.

There is another part of me that thought of selling the the 2 family and using the capital to buy land and building multiple units up north or buy a couple condos.

Are there other options I'm too much of a newb to think of ?

Thanks John