If you're worried about the seasonality of the Dells area and filling vacancies during "off times" aka winter.

At the beginning of every winter season, I send a message to the tenants with the account information and let them know to call the gas company if the heat goes out.  

Searching to see if any lenders are doing a cash-out with no seasoning period. 

For whatever it is worth, we rent our STR by the month during the non-tourist season and we have a walk-through video on YouTube.

Tread lightly there as NY/NYC is a market for seasoned investors so you need to be able to see some of the schemes the buyers (and agents) will try to pull on you early on (too many to list).

Someone experienced and seasoned, who can hear my plans and goals and give their take on how to reach them, or offer new ideas. 

I understand the intent behind the law, but most investors will find ways around the law, or just opt out.This is a question for a seasoned attorney in the market.

Lastly, the real attraction here is the 10-12 week summer season; usage the rest of the year would just be gravy to some.

I prefer the cleaners coming closer to the time of the next guest than immediately after the last guest leaves (normally this is only an issue during our slower season).  

Hello @Shelby,Turnkey is always a great option for new and seasoned investors as it requires minimal time and effort, as they come fully renovated and often with residents in place.