You know the phrase, "too many cooks in the kitchen"? 

You shall never pour cooking grease or other damaging/obstructing objects down toilets, sinks or drains.

We built it up to 4 STR and were cooking with gas until BOOM -- The city we live in changed the laws around STR and Abnb and made rentals under 31 days basically illegal.  

I have an acreage in a quite a desirable tourism area - minutes to a large lake, amenities and tourist attractions all around and the property has amazing lake views.The thought here was to setup a glampground essentially - as the zoning allows for 10 fully serviced sites and provide renovated units in a private, comfortable setting.For example, a modern updated travel trailer, hot tub, fire pit, great cooking amenities in individual private areas .

I agree with @Ethan Cooke that you may want to look into CBIZ or another company that offers commercial liability insurance for short term rentals.

The market changes constantly based on outside variables (G.I bills, oil embargo, pandemic, war, dot-com bubble, etc.).

Too many cooks....That leads me to number 2 - You have to check the HOAs financials.

I would just invest it in an oil and gas mineral rights royalty fund and receive a truly passive 8-10% annualized cash flow.

Manaseer I actually live and own a multifamily in glenview and I'm in the process of rezoning one of my properties to build a 8-10 plex but cook county is being difficult as I'm sure anyone that lives here would know.

Tyler Cook