@Kash Tacke I'm a big fan of ADU's in general especially here in the mid west, yes you could potentially be on the front of the wave, but housing density is the solution to the affordability issue, anytime you are investing with affordability in mind is a great strategy to me, and sound like there are some incentives or at least supporting winds form the local city, that in itself seems like it would be worth at least approaching an architect or contractor to bid up some plans or concepts to take tot he city.  

If it's on the higher side you may want to consider it for mid-term or long term rental, but if most stays are below 30 it can be viable for short-term! 

Sara, Just very slow this year in long and mid term.

Quote from @Kody Smith: without getting too deep into my finances, what my strategy is...1. take loans to buy properties (leverage)2. fix/flip for day to day cash flow income3. use some of the fix/flip income to buy consistent cash flow through:- business acquisition, - commercial properties (MF and store fronts),I have no intention of doing ALL of the management myself, I will hire management as needed (medium term goal)my expected core role is money provider, evaluating the numbers, making decisions, and connecting with investors, wholesalers, lenders, contractors, and property owners.while I am just on step 2 of the journey, I am looking toward step 3 to stabilize, and not worry about if house prices drop mid project or not (or not worry as much) So to be fair this is more about obtaining and growing a real estate business not simply buying rentals for cashflow.

Do you know if this would be an issue when it comes time to having my 5 year DCA inspection in ( mid 2025) as the property is only register with them as a 4 family?

If you're open to mid term renting (we transition to this during our slower season), I'd also recommend speaking with the university and trying to see if you could try to be the source for their mid term housing.

I also wonder if some hosts only list during football season and then transition to mid-term rentals (MTRs) the rest of the year.New Tax Changes Coming in January 2025Starting January 2025, Airbnb will automatically collect and remit the 5% tourist tax for Gainesville.

With the upswing in the country's short-term and mid-term rental markets, a unique opportunity is presenting itself to house hackers during a time when it's harder to cash flow than it was a few years ago.

Evenings aren’t possible for me since I work mid shift, unfortunately.  

Closed mid-December and was able to get two bookings for the holidays.