You don't stop to think while you're in the middle of starting any endeavor about how much you've learned. After almost 15 years of owning and managing vacation rental homes, I've learned a few things. You try something, make mistakes, learn how to do it better, try something new, make more mistakes, learn something new...and repeating the cycle over time, you learn a great deal. I didn't realize just how much I'd learned until friends of ours wanted to get into the vacation rental business and asked me for my advice. Together, we looked at properties and I gave them advice on ones that would make good rentals vs. others and features they should add to maximize their marketability. I also advised them on types of furnishings to include, how to position and promote their property online, the art/science of setting rates and fees, how to use local property managers, navigating the world of sales tax and business licenses...The net result was that they were able to get their property up and running in a few short months and are off to a great start. Their rentals already have exceeded their initial projections and are enabling them to operate profitably month to month. It literally took me years to get my first rental to that same place.