Just avoid self-dealing and follow IRS rules.

There are specific rules on when rent increases can be submitted for review, but there are no guarantees when they will respond.

I also saw a blog post by the Financial Samurai that said if he could sell a rental for more than 100x the monthly rent, he should... but I wasn't sure if others liked that as a general rule? 

Hi Max, a good rule of thumb is to start with your target market/ideal guest.

Quote from @James Hampton: That's a bad practice to follow.If an occupant is not named on the lease, you may have difficulty enforcing rules or evicting them.

The STR owners have banded together and are meeting with the town as a group, and it looks like the town will adopt some STR rules allowing and setting guidelines for STRs. 

Are all units identical? 

Hey @Joel Oh, so let's clarify the NYC rules around STRs.STRs are legal in NYC as long as these directions are followed."

You don't ever want to double book and have to cancel one of them.And the guest giving a phone number in the first message like in your original post is against the rules and the guest knows it. 

They also handle legal matters, like making sure the property follows the rules or dealing with evictions if necessary.For finding deals, I recommend starting by connecting with investor-friendly agents in your target market.