Pick areas that you know either having had lived there, visited family, been on holiday.

@Oleg Serdyuk I agree with @Marc Winter.

Generally speaking prices are better in the winter, but it is also harder to find tenants at that time of your.

Winter is getting boring/old as one is forced to come down to Az to live.

A summary of my local region is: major summer tourist destination, slow winters.

After I have experienced the summer in the south I am happy to put up with the winter here!

The surface of the roof is ~5500 ft sq, and the building is in a cold climate (nice summers, snowy winters). 

If you don't want the hassle of running the business, why not fill in for other dentists so they can take holidays?

The heat doesn't work properly in the winter (which we managed to get through) but the unit makes some crazy screeching and thumping sounds with the AC running, especially in the middle of the day when it's so hot you can fry an egg on the sidewalk.

I've seen leases where the tenant gives itself rent holidays in later years of the lease.