Hey @Cosmo Iannopollo all good things on this thread! My 2 cents:
-tax considerations - some municipalities charge "lodgers tax" just like a hotel, some dont. Do your homework.
-rules/regs - this one is huge, already been address on the thread. Start with a google search or post a search in the Airbnb community forum or on Bigger Pockets. Someone on here is bound to know the regulations
-dealing with neighbors - In Denver this is the #1 way to get your license revoked. In metropolitan areas I think it is a worry that STRs change the "character" of the neighborhoods. I always like to be as upfront as possible and tell your neighbors exactly what you're planning to do. Better to find out before you buy the place that they hate Airbnb than after you've closed and spent a ton of money.
Lessons Learned:
-Be extremely selective as to the location of the property (I took on some regrettable properties when I first started)
-If you are self-managing, be prepared to make a lifestyle change with multiple units
-Educate yourself as much as possible before you start hosting so you don't make costly mistakes. I missed out on thousands in revenue when I first started by using Airbnb's smart pricing tool
-Put a lock box somewhere on the property for when your digital lock runs out of batteries or malfunctions
Hope this helps!