hi we are thinking about turning our primary house into a short term rental (have lived for two yrs) and getting a new primary near by (10 min away different city).

My partner and I are going to send out handwritten letters to home owners in our nearby city.

There are much more business friendly states nearby, believe me :)

Look at surrounding areas like Port Chester (though taxes might be higher) or another nearby area with lower priced houses 3.

They sound small, so it's likely that there aren't brokers focused only on them, but rather will be covered by brokers in nearby larger cities, especially since you are talking about commercial properties like hotels and multifamily, and these tend not to be handled by your local residential brokers.  

We live in a B class suburban neighborhood in the Midwest and are under contract to purchase a property in a nearby C+ neighborhood (closing in less than 48 hours.)

Another strategy is finding a nearby similar place for rent and acquiring about the rent.

I was told that I could do this since the house was in a resort community and not nearby to my home. 

For some reason this home wasn't selling & we were assuming light pollution from a near by college could be why.

This may be attractive as the lake & mini grocery store is near by and we have clean fresh air.