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.

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.

In the unlikely event that you are the exception that proves the rule, the rare 18 year old who can actually generate a serious income by wholesaling real estate, your day to day will look like the following: - You will door knock, cold call, send mailers, and otherwise create lists of people who are in the most desperate moments of their lives. 

It seems simple, but it's not a DIY thing because of technical rules that are different depending on circumstances.Or, you can pay a lawyer to file an ejectment lawsuit, the developer can pay a lawyer to defend the lawsuit and redeem, and the developer will also be responsible for reimbursing your legal fees, plus interest. 

For suburbs you really have to search for each cities rules.  

Since you missed the 2 out of 5 rule, capital gains taxes might take a chunk of your profits, so consulting a CPA would be smart to understand how much you’d actually keep.

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