Then, the issue has already been addressed by the state/county/city, I know what the deal is, and it's unlikely to change (or at least change dramatically) - the gov't is already getting their cut so they aren't likely to mess with a good thing.It seems that urban areas are the riskier ones from a regulation standpoint, but from a cash-flow perspective they can be more reliable because of the variety of travelers they cater to, not just tourists.  

That area is very nice close to Sarasota beaches and tourist areas with reasonable home prices similar to the Aurora/Batavia area, which you are familiar with being from Naperville.

-Tourism - there are some areas of the country that will almost always stay busy, and have high demand for hotel/motel/airbnb due to it being a major tourist area. 

I went to PDC last week for 5 days and staying on 5th Ave and 30th St (tourist area).

There is so much regional demand even Mexico is building massive new high rise residential (self contained mini city) and medical tourist complexes walking distance to border (100 feet). 

ATypical Type of Anchors: Anchor-less or a small convenience store anchor.Trade Area Size: <1 mileProperty Type: Power CenterConcept: Category-dominant anchors, including discount department stores, off-price stores, wholesale clubs, with only a few small tenants.Typical Type of Anchors: Category killers, such as home improvement, discount department, warehouse club and off-price storesTrade Area Size: 5-10 milesProperty Type: LifestyleConcept: Upscale national-chain specialty stores with dining and entertainment in an outdoor setting.Typical Type of Anchors: Large format upscale specialtyTrade Area Size: 8-12 milesProperty Type: Factory OutletConcept: Manufacturers' and retailers' outlet stores selling brand-name goods at a discount.Typical Type of Anchors: Manufacturers' and retailers' outletsTrade Area Size: 25-75 milesProperty Type: Theme/FestivalConcept: Leisure, tourist, retail and service-oriented offerings with entertainment as a unifying theme.

Most areas have higher traffic times a year especially in northern climates but it is not just tourist areas that do well for AirBNB. 

I live in a rural tourist city that is hyper nazi about signs.

Likely clients will indeed be parents/families in town for university events, visiting academics and artists, tourists, etc.

Lake Mary is nice, much nicer than the rat race of tourists down by the parks.