Airbnb Newbie Advice Grab-Bag
Some thoughts, in no particular order:
First and foremost, check city and HOA regulations. If they're not friendly to this use, you can try to wing it for a while, but there's a strong chance the rug will get yanked from under you after you've committed to this business. If they're good with it, make sure you understand your city and state requirements for registering your unit and paying hotel tax, as that'll be something you'll need to do.
Make sure your location REALLY lends itself to STR use. If you're super packed in with neighbors, some of whom are weird or hostile, and you're targeting a lower-end guest mix who'll throw parties or bring hookups home or whatever, it's a powder keg. On the other hand, if the place is on a generous lot giving good separation from neighbors, and you're pricing and screening to attract more stable guests, you'll do much better.
You'd rent the whole house, and not be living there while hosting guests in rooms? I really think the former is the way to go; you'll see tons of problems in this forum tying back to hosts trying to share space with guests.
People are making great points about cleaning and laundry. With 3+ bedrooms, laundry will take longer than cleaning. Even when I have my cleaners turn a house, I go there with my laptop afterward and catch up on email while running the last couple loads of laundry.
Doing your own turns can be a great source of extra income; depending on your pricing, it can, for example, turn a $150 night into a $250 night (if you keep the $100 cleaning fee). I have a pro cleaning crew but have started doing occasional turns myself when they're easy (e.g., 1 or 2 people for 1 night). I leave the big jobs to my regular crew.
Get 3 sets of sheet per bed - that way you can strip the beds, immediately remake them, and have spares if there's a bad stain. You'll want white sheets so you can bleach out stains. Having the same size beds (e.g., queen) in all bedrooms helps laundry go faster. One of my places has a king, two queens, and a full, and it's a pain to tell which fitted and flat sheets are which when they're all white.
You don't really need to "insure the business" as much as you need to make sure the house's insurance policy allows STR use - your dad may need to switch carriers to get this. Also, he should think about a legal structure for holding the property in order to minimize liability should someone fall off the porch and break their leg and sue or whatever. Also, you probably want to set up your business as an LLC to similarly limit your own liability. A good accounting firm can get you set up well here.
I find it pretty easy to keep my own books in a spreadsheet - I also use Quickbooks as I have other real estate stuff, but it's very expensive and IMO overkill for 1 STR property. Just log your income and expenses as they happen (or within a day afterward) and categorize them in a way that makes sense (Repairs, Consumables, Taxes, etc.). Also learn to differentiate between capital expenditures (furniture, big repairs, etc.) and regular operating expenses.
Once your listing is stabilized on Airbnb, you should strongly consider getting your place on Booking.com. I recently added Booking to my mix and it quickly moved way ahead of Vrbo as my second strongest platform. I realized this is because it places it right next to actual hotels when people are searching in my town - i.e., a business or weekend traveler is looking for a hotel, and the results they get are the Holiday Inn and my houses. It's hella powerful. It's also a lot more complicated to set up than Airbnb, so I suggest you get fully up and running on Airbnb first and then in a few months extend to Booking.
Finally, it's near impossible to be instantly profitable with this, but the bookings do happen and the money does roll in. There are hundreds of little lessons to learn, but if you take the stance of an empathetic host seeking to give a great guest experience, and you learn from every stumble and adjust your systems to do better next time, your numbers will look better in time. And you'll learn a ton about business.
Good luck!
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