Least Favorite Parts of Owning/ Operating a STR?

[Tyler Solomon]

I am certainly one of the bigger proponents of STR's, but I do think it is important to keep in mind that these are assets which require creativity, upkeep, costs, and a whole lot of TLC. With that said, I think it is important to highlight the pain points of Short Term Rentals that often get glossed over by new and experienced investors, or those looking to get into the industry. So I ask...

What are the biggest pain points of operating a STR? What are the unforeseen challenges that you have encountered ? What are the nitty gritty parts of operating a successful STR?

Feel free to bring others into the conversation!!

[John Underwood]

Mountain Cabin well operating slowly for a few weeks in the summer.

Lake dock needing to be moved out when there is an ongoing drought, then back in.

[Michael Baum]

For us, maybe checking to see if anything is broken or missing. We have a lot of amenities and it is easy to miss a broken glass or stolen waffle maker.

[Andrew Steffens]

As ex-Army Infantry/Drill Sergeant it is whiny guests.  I know it comes with the territory and we do 300-500 reservations per month so the law of averages apply but people demanding a 50% refund because the wifi went out for 2 hours after a Florida summer thunderstorm and then trashing your review because they did not get their unreasonable request granted is the worst.  Knowing this is my weak spot (customer service to unreasonable guests) I hired department managers from the hotel world who were already trained to deal with this type of thing. 

[Tyler Solomon]

Quote from @Andrew Steffens:

As ex-Army Infantry/Drill Sergeant it is whiny guests.  I know it comes with the territory and we do 300-500 reservations per month so the law of averages apply but people demanding a 50% refund because the wifi went out for 2 hours after a Florida summer thunderstorm and then trashing your review because they did not get their unreasonable request granted is the worst.  Knowing this is my weak spot (customer service to unreasonable guests) I hired department managers from the hotel world who were already trained to deal with this type of thing. 

 Great move on the outsourcing! Know your weak spots and adapt!

[Leslie Anne Morris]

Consistency in guest communication, being out of state and unable to be hands on, nuances that come up that you were completely unaware of and you don't have strong boots on the ground - all good reason to be passive in this business.

[Brian Barch]

Maintaining good cleaners

Debating whether to stay in the cabin ourselves for holidays, or rent as those days are lucrative.
having to pay for a cleaning crew for personal stays. Yes we could clean ourselves, but elect not to with 3 young kids.

In general, all the things that could go wrong for a guest, things that are unacceptable when paying as as a guest (internet outage, clogged drain, etc)

The anxiety of managing to positive reviews in the early days when one bad review can do you in

Unknown and changing legislation 

[Matt Mertz]

1. General anxiety when something goes wrong.

2. Staying in your own wonderful STR and never getting to enjoy it because of maintenance or improvements. It's an ongoing joke between me and my wife.

3. I was going to mention uncommunicative cleaners but we found a wonderful replacement after our original cleaners quit on us.  A blessing in disguise.

[Dan H.]

>Unknown and changing legislatio

This is definitely my least favorite.  We have 2 STRs that we have had as STRs since 1999 that have to win a lottery to continue as STRs.  Note we have paid the taxes, etc that were required.  In summary, even though we have followed the ST3 rules and paid taxes, the future of our STRs rely on winning a lottery. 

If we win the lottery, do we have any assurance that STRs will not be further reduced or Eliminated all together in the future?  I would think not if they can arbitrarily eliminate STRs that have legally existed for 23 years.  

[Gerald Pitts]

Self managing.  90% of the time or more it's a breeze.  But you're technically on call a lot of the time.  

[Luke G.]

Whiny guests, 10% of the guests take up 90% of my patience.  Complaining about bed bugs when it turns out it was a tick (in the woods shockingly), showing up 2 hours before actual check in and complaining the fridge isn't cold (was being defrosted), wanting a refund because a light was burned out in the hallway etc.  I can handle everything else, most guests are great but man the bad ones are...bad.