See if local regulations permits this first, then search on Vrbo and Airbnb to see if there are any sucessful properties in this area.

I previously worked with a contractor to help with permits and drainage since there’s a possible wetland issue, but unfortunately things fell through between us and I didn’t make progress. 

I allow for tenants to use gas fireplaces, but do not permit tenants to use any wood burning fireplaces.

I know johnsburg you can’t do an str at all fox lake and lake county yiu need permits.

In short, if you're not renting every week of July-August and every weekend of the winter, you're taking losses, particularly given the ridiculous prices I'm seeing new investors pay farther north in vacation areas like North Conway or the White Mountains.And looking solely at North Conway's recent court case is a red herring: plenty of small towns around the NH continue to enact knee-jerk reactions and excessive permitting/regulations as a reaction to STRs assumed role raising housing prices and shrinking supply for local residents.

Their requirement for permits differed from what the law requires.

I did mine when I was in the timber industry.. it was common for me to log a property then sell said property to buyer on contract.. but they had to go through the building permit process and in Oregon that can take a year or two.. so I would sell on contract.. then take my contract to my trusty commercial banker and hypothecate it..

VERY expensive to build these and getting permits very tough ..

Although we weren’t changing the exterior, we were asked to provide a survey of our property, elevation drawings, stamped FAR calculations, and sat in front of the city councils to obtain an approval (the special permit).

The past couple years they have been tightening up on giving permits for STRs but this year they have the jubilee happening so they haven’t been as hard on it but that could easily change after especially with the move Spain just recently announced and Venice and Florence are cutting back as well.