My wife and I bought our first vacation rental/short-term-rental in September of 2017, after almost a year of searching, submitting offers, negotiating, performing inspections, withdrawing offers, and repeating. By the end of the search, we had changed target markets, bid on three houses, had offers accepted on two, withdrawn one for inspection issues, gave up on the project before becoming re-inspired, and, finally found the house we always wanted but didn’t quite recognize at first. In the four weeks after closing, we made some crucial safety, amenity, and cosmetic updates with guests’ experience first in mind. After beginning our venture, we rented our house out every weekend except one throughout the first six months (with only a few weekends set aside for ourselves), until we closed down for a few weeks in the spring to perform some additional upgrades. In all we’ve had dozens of bookings, almost entirely 5/5 star reviews, and have become an Airbnb Superhost and HomeAway Premier Partner. Right now, we’re looking patiently for our next STR property. In the meantime, we enjoy staying in others’ vacation rentals, and have very quickly realized some have gotten it 100% right and some haven’t even come close. We want to provide to others the kind of guiding principles, shortcuts, and tips that we wished we had had while purchasing.