Even with rent control it's still better to be a landlord of a long term tenant than follow the licensing restrictions. The license 1) Costs money and 2) limits the number of days you can rent.
#2 is the big issue. Even with rent control, at least you can rent the place out for the whole year. With the license you can only rent the place out for 90 days a year. You must live in the unit the other 275 days of the year. So your rent controlled rate would have to be 25% of market rate for the legal short term rental to make sense, and you'd have to live there when it isn't rented.
