Where should I house hack?

[Benjamin Yagiela]

I recently accepted an offer for a SaaS account executive position and it's completely work from home. Currently, I live in Sarsasota, FL and want to move to an area that I can have max potential for house hacking a duplex or triplex in an up and coming area. 

I like to trail run, snowboard, hike, and appreciate a good night life with comedy clubs and music scene. Out west is great but highly saturated from what I have gleaned. I am originally from Michigan and would be open to moving back to be closer to family but open to all areas as well.