Looking back, my biggest rookie mistake was cheap furniture that didn’t survive the first year. 🫣 Learned that lesson quick. Curious — what’s yours? Might help someone else dodge the same headache!”
Keep your Airbnb finances separate from your personal finances. Keep track of your expenses and also pay yourself. This will help with the tax bill at the end of the year. I've been using Baselane for this, it has saved me hours of time.
Totally agree — keeping STR finances separate is huge. I haven't used Baselane yet but I've heard good things. Do you feel like it's better than just a regular business account?
I personally do, I have 2 properties: both a long term rental and an Airbnb. It makes managing multiple properties very easy, also it has a high yeild savings which I love! I did a lot of research before choosing Baselane and it's been amazing.
I personally do, I have 2 properties: both a long term rental and an Airbnb. It makes managing multiple properties very easy, also it has a high yeild savings which I love! I did a lot of research before choosing Baselane and it's been amazing.
I keep my business finances in a spreadsheet. All my properties pay into a business account and it pays the business bills.
My Attorney and CPA agreed that I have too many properties to have seperate accounts for.
My CPA also tells me every year I am one of his most organized clients.
Did you have separate bank accounts set up for separate properties?
Using the "class" function in quickbooks to categorize transactions based on which property it should be associated with is the best way I have found to keep track of everything
I keep my business finances in a spreadsheet. All my properties pay into a business account and it pays the business bills.
My Attorney and CPA agreed that I have too many properties to have seperate accounts for.
My CPA also tells me every year I am one of his most organized clients.
Did you have separate bank accounts set up for separate properties?
Using the "class" function in quickbooks to categorize transactions based on which property it should be associated with is the best way I have found to keep track of everything
One businesses account for all properties. My attorney and CPA both agreed I didn't need a separate account for each property. I would need too many accounts.
I keep my business finances in a spreadsheet. All my properties pay into a business account and it pays the business bills.
My Attorney and CPA agreed that I have too many properties to have seperate accounts for.
My CPA also tells me every year I am one of his most organized clients.
Hi John,
I'm curious to knw if you ever tried Quickbooks for keeping your properties/expenses/repairs etc straight? I'm wondering if you vetted it, and if so why you felt it wasn't a good fit.
I keep my business finances in a spreadsheet. All my properties pay into a business account and it pays the business bills.
My Attorney and CPA agreed that I have too many properties to have seperate accounts for.
My CPA also tells me every year I am one of his most organized clients.
Hi John,
I'm curious to knw if you ever tried Quickbooks for keeping your properties/expenses/repairs etc straight? I'm wondering if you vetted it, and if so why you felt it wasn't a good fit.
Accountant · Chicago, IL · Member since 2018 · 2k+ posts · 1k+ votes
1y
on the tax side, maintaining a time log is crucial. Understanding what's needed to maintain compliance with STR loophole regulations. Having this documentation is crucial in the event of an audit
Love hearing this — organized books make tax season so much smoother! I’m the same way — I keep a clean spreadsheet and a solid business account flow. Makes it easy for my CPA and keeps surprises away.
Love hearing this — organized books make tax season so much smoother! I’m the same way — I keep a clean spreadsheet and a solid business account flow. Makes it easy for my CPA and keeps surprises away.
I enjoy tax preparation season getting everything ready for my CPA.I usually spend a couple days going through everything and my spreadsheet automatically adds up all the different categories per property.
I go through all by bank and CC accounts making sure I didn't miss any deductions.
One of my counties doesn't charge a CC fee when paying for property taxes. I put these on my business CC that pays 2% back, then I pay off the CC right away.
So true — a good time log is gold when it comes to the STR loophole. It's one of those things you don't think you need… until you really do. Thanks for pointing it out!
Investor · Florida Panhandle/Illinois · Member since 2016 · 4k+ posts · 3k+ votes
1y
I use an excel spread sheet. I have multiple properties and I describe each expense and revenue source in the description column. It took a few years to get this correct, but it works very good. My accountant rarely has to call me about an entry.
I make sure I update entries at a minimum each month.
Real Estate Agent · College Station, TX · Member since 2025 · 6 posts · 4 votes
1y
MAKE YOUR LISTING UNAVAILABLE WHEN FIRST PUBLISHING ON AIRBNB
I cost myself $1,000+ with the first airbnb I set up.
When publishing a new listing on airbnb I have found that not all of the relevant settings are a part of the initial setup. Because of this my property went live without a cleaning fee attached and without proper pricing.
Using a third party pricing software like PriceLabs - the property has to be published before it can be synced.
Because of this my first property was WAY underpriced and before I could get it synced to pricelabs (within 2 hours) someone booked it for one of the busiest weekends of the year for a fraction of the cost.
Ordering anything from Wayfair. Wayfair is not a retailer with their own warehouse(s). They literally scrape the internet for anything that looks like furniture and homewares and make their own listing for it. While you think you are buying it from Wayfair, in reality they are the middle man who buys it for you from another site with a hefty markup.
You can get around this by doing a reverse image search to see where they actually get the product from.
On a related note- anything that requires assembly is a net loss. You still have to pay someone to put it together, or do it yourself, which either way will bottleneck your setup. By the time you figure in the cost of time/labor you could’ve bought a higher quality item with no/less assembly required. Buy something with zero or at best minimal assembly.
Interior Decorator · Chicago, IL · Member since 2025 · 31 posts · 40 votes
1y
Oof, the cheap furniture one is so real. I’ve seen that mistake cost more in replacements and bad reviews than just starting with durable pieces in the first place.
For me (or for some of the hosts we’ve worked with), a big rookie mistake was not thinking through functionality for guests. Like no spot to put a suitcase, nowhere to hang towels, or not enough lighting in the bedroom.
It’s those little overlooked things that show up loud and clear in guest reviews.
Designing for how people live and move through a space is just as important as how it looks!
I also 100% agree that the financial aspect, mentioned above, is way more important, but coming from a design aspect, flow is important!
Real Estate Agent · Vienna, VA · Member since 2015 · 8 posts · 1 vote
1y
I think close to not cheaping out on furniture, also don't skimp on good thick bath towels. Costco sells good ones that are not too pricey. My cleaners recommended dark colors vs white because they do hide stains a little longer. Yet another thing that shows up on the guest reviews that is easy to fix!
Good point — Wayfair is definitely a middleman a lot of people don’t realize. Reverse image search is a great hack! I also agree on the assembly — been there, done that, learned my lesson. Paying more upfront for ready-to-go furniture saves so much time and headache on a setup.
Rental Property Investor · Arlington, TX · Member since 2016 · 706 posts · 611 votes
1y
Got a property where the HOA didn't allow for STR, so I had to turn the property into a mid-term rental with little clientele. It was a valuable learning experience, and I have successfully made midterms my primary target when acquiring new properties. I ultimately completed a 1031 exchange on that property, which has significantly boosted my business.
Absolutely — so true! I’ve learned (and seen) that the small functional details make or break a guest’s experience. A beautiful space that’s inconvenient is still going to get dinged in reviews.
It’s the hooks, luggage racks, good lighting, and smart layout that turn a nice stay into a repeat booking.
Great point about balancing the design with real-life flow — totally underrated!
Absolutely — thick, quality towels are such an easy win and guests always notice! Darker colors are smart too — saves everyone headaches with stains. It’s the little comforts like this that really add up to better reviews and repeat stays. Great tip
Thinking that Airbnb has your back. They don't. The owner is the lowest in their eyes. Any problems I ever had with a client, Airbnb was useless and did nothing. I've had imposters enter my property that were not the people that booked. No help, zero!! Once when I had to cancel a booking (3 weeks in advance) because I had to leave the state, they attempted to make me pay for the cancelled persons new accommodations in full, unless I could show proof. Airbnb is awful.
Thinking that Airbnb has your back. They don't. The owner is the lowest in their eyes. Any problems I ever had with a client, Airbnb was useless and did nothing. I've had imposters enter my property that were not the people that booked. No help, zero!! Once when I had to cancel a booking (3 weeks in advance) because I had to leave the state, they attempted to make me pay for the cancelled persons new accommodations in full, unless I could show proof. Airbnb is awful.
Thinking that Airbnb has your back. They don't. The owner is the lowest in their eyes. Any problems I ever had with a client, Airbnb was useless and did nothing. I've had imposters enter my property that were not the people that booked. No help, zero!! Once when I had to cancel a booking (3 weeks in advance) because I had to leave the state, they attempted to make me pay for the cancelled persons new accommodations in full, unless I could show proof. Airbnb is awful.
Boulder, CO · Member since 2023 · 169 posts · 95 votes
1y
@Travis Piper Lol. Made the same mistake except with VRBO! I didn't know that Instant Booking is the default so when we went live (and I hadn't finalized pricing several months ahead for the Christmas Season), Christmas booked instantly and I turned it off immediately once I realized what had happened. Not a fan of Instant Booking because I can't vet (even if just assessing how well communication is going to go).
I don't think this is just a rookie mistake but QR or independent quality reviews are really helpful if you can do them. I can't do them consistently but every time I've done them, I can see what's been dropped or what can be improved. (Our cleaner is usually excellent but if she sends someone else out, it's not as consistent.)