Regina, hi. In regards to the crackdown, I think the city/county is probably looking where people are complaining. Areas like Kailua are especially vulnerable due to the community conflict regarding BnBs. I also think that enitre homes that are rented out are easier to find than a home where the host lives and rents out a room. Nonetheless, we are staying alert to possible public agents seeking to find our spot. Overall, I do think, as things stand now, that the odds are in our favor that we will be able to maintain the room rental.
We are waiting to find out what occurs with the state/airbnb issue before paying our tax. Once we file our TAT and GET tax we become vulnerbale to the city/county, if they wish to shut us down. Id rather pay to AirBnB and maintain anonymity. The city/county has not offered bnb licenses since 1990, at least that is my understanding. I can't imagine that the city/county would openly agree to allow AirBnB as that would set precedent and therefore encourage short term vacational rentals, which the city/county have fought to limit.
If you live in an area where you seldom interact with or see you neighbors or,
If you live in an area where you and your neighbors are friendly and they like you...
If you live in an area where there is plenty of safe street parking or if you have an extra parking space that is 'out of sight, out of mind' to your neighbors....
If you check guests in at times when your neighbors are at work...
If you prep your guests by asking them to say that they are friends visitng...
If you stay alert to booking requests from people that live on Oahu, which will seldom occur, if at all....
Then you should be fine.
We have hosted AirBnB for 4 years and its been great. We really enjoy the guests as they are always excited to be in Hawaii. Our guests are usually on the move and we only see them when they leave in the morning and return at night. In essence, they are the best roommates...the kind you seldom see and when you see them they are happy.
The downside to AirBnB is that, although it helps us afford to live in this expensive place (Oahu), it does exasperate the high cost of rents by further reducing available rentals. Supply and demand...
When is the North Shore gathering. If I can make it, I will attend:)
~Sean