How do you all stay on top of STR permits/rules across multiple properties?

Question

Hi fam!

I’ve got a few short-term rentals across a couple of different cities/towns with STR compliance regulations, and I struggle with keeping up with all of it

It’s not any single thing — it’s that every jurisdiction does it differently. Different permit renewal dates, different lodging tax filing schedules, different rules about what has to be posted on the listing, and they all seem to change the rules every year. I’m currently tracking it with a messy spreadsheet and calendar reminders I set myself, and I always have a low-grade fear I’ve missed something that’s going to cost me a fine or get a listing pulled.

So I wanted to ask the people who actually do this at scale:

• How do you track permit and license renewals across multiple cities/counties?
• How are you handling lodging/occupancy tax filing deadlines?
• Has anyone here actually been fined, warned, or had a listing flagged for a compliance miss? What happened?
• Have you found any tool or system that actually works for this, or is everyone just on spreadsheets?

Trying to get a sense of whether I’m overcomplicating this or whether it’s genuinely as messy for everyone else as it is for me.

Thanks for your help!

Curtis Peck · Answer

Yeah, you're not overcomplicating it. Every multi-city STR operator I've  talked  to is fighting the same thing, and the spreadsheet is where most of them end  up  because no single tool does all of it.

For lodging taxes, Avalara MyLodgeTax is probably your best bet. They file in  most US jurisdictions and run the calendar for you. Not cheap, but it's the  closest to a real solution.

For permits and licenses, everyone ends up on a tracker with reminders set at  60, 30, and 14 days out. That's the only thing that consistently works.

The "rules keep changing" piece is the one most people miss. You can set up a  page monitor (Visualping or Distill.io) on each city's STR ordinance page.  It'll  ping you the second they update anything. Underrated move.  And yeah, people do get fined, mostly for lapsed renewals. The listing pull  hurts way more than the fine.

If you want to dig into any of this, shoot me a message. Happy to point you in  the right direction.