While a small city, it is only 30 minutes from the capital of WI so it is becoming a very popular suburb.

@Joel Owens and @Mark Creason can help hereTenant-In-Common investment properties (generally syndicated, and not as popular after the recession) Delaware Statutory Trusts (DSTs) (generally syndicated, much more common after the recession)There are pros and cons with each type of investment opportunity, so make sure that you do you own due diligence. 

If it doesn't exist in the average popular vacation spot on Airbnb or TripAdvisor then I assume it probably doesn't exist at all.

It is easier and more popular, but not better.

With a rental, you will definitely want a rental property policy to help protect you from liability in the event that a tenant gets injured, etc.

I have a house OOS in a popular market and on the edge of popular zipcode within the area.

Or if you're injured for example and can't work for 9 months...  

We've just listed the property in the past couple of weeks and so far the bookings we have received are:2 whole house bookings (one for 4 nights & one for 2 nights)2 lower apartment bookings (each for 2 nights)0 upper apartment bookingsMaybe the lower apartment will be more popular than the upper one because most people are only coming for a weekend & don't plan on cooking anyway, and it is less expensive than the upstairs apartment.We'll see....time will tell.

Westside Rentals is becoming very popular in Los Angeles.

I really got a lot out of the Serge Shukhat multi family episodes,  Show 60 and  Show 131 .I recommend the Shawn Holsapple wholesaling episode,  Show 136 all the time.I really liked the Zeona McIntyre show about AirBnB,  Show 229 .Swanny's show about investing in real estate on a teacher's salary was a very popular episode,  Show 238 .Scott Trench's episode about House Hacking and Frugality is our most popular interview,  Show 223 .