Be sure you check the local regulations regarding what you can rent out in what zoning for what time frames, there are restrictions in Vilas and Oneida counties and possibly others, recent state law changes have forced changes to local ordinances, but there are special requirements either in the works or already in place, for the most part in Oneida county you can not rent a property in residential zoning for less than 7 consecutive days unless you have appropriate licensing from the county. this may also be the case in Vilas, prior to state law change it was 30 days, this was to protect resort owners and near by property owners from an owner that wants to run a VRBO weekend packages and have people loud and obnoxious at their lake house all summer.

If you are interested in getting involved with the coalition, we are holding an event on the morning of September 10th at Turning Stone Resort.

Being a landlord is stressful for me, so I would most likely resort to using a property management company.

LONG GOALS: My passion and dreams are to be a real estate investor, and ultimately own wellness/well-being resorts that you don't have to know Gweneth Paltrow to be able to access or afford.

@Andrew Stein I'm in Orlando and we have resort/vacation/STR only communities that are specifically used for STR. from condos to townhomes and 4-14 bedroom single family.

I'm wondering if there are many people out there who do airbnb arbitrage in the mountains and at ski resorts?

The players are only a few people - not enough to make a notable difference on the local economy. 

Hey @Kris Kempe - The easiest way is to partner up with another Chicago wholesaler who has their license or get your license yourself.Getting your license yourself is smart no matter what, but if you wanted an intro to some of the bigger players here in the city I'd be happy to make an intro for you.What city in Illinois are you in?

I have a friend, pro poker player - he sits at the table with high stakes and STILL cant HODL Bitcoin.

I purchased my condos in a building that doesn't have a resort manager onsite.