What would you do differently if starting from scratch?

Category: Off-Topic & Lounge

By: Anika Sharma

Posted: 2026-02-11T06:48:59.161Z

For experienced hosts (2+ years): if you could go back to Day 1 and start your STR business over, what would you do differently? What mistakes did you make that you wish someone had warned you about?

Reply by Megan O'Connor:

5 years, 8 properties. Here's my "start over" list: **1. I'd invest in professional photos on Day 1.** I used my iPhone for my first listing and underperformed for 3 months before getting pro photos. Revenue jumped 40% overnight after upgrading to professional photography. The $300 I "saved" probably cost me $3,000 in lost bookings. **2. I'd buy PriceLabs immediately.** I manually priced for my first year — staring at competitors, adjusting nightly. Dynamic pricing through PriceLabs (https://pricelabs.co) increased my revenue 15-20% AND saved me hours of work weekly. $20/month per listing is the best ROI in STR. **3. I'd set up an LLC before my first booking.** I operated as a sole proprietor for 18 months before forming an LLC. If a guest had been injured during that time, my personal assets would have been at risk. An LLC costs $100-500 to form depending on your state. Do it before you start. **4. I'd start with a cleaning checklist, not a cleaner.** My first cleaner was my neighbor's daughter. No checklist, no standards. Guests complained about cleanliness. Now I use a 50-item checklist with photo verification through Turno (https://turno.com). Start with systems, THEN hire people to follow them. **5. I'd buy STR insurance from Day 1.** I relied on AirCover for my first 2 years. Then a guest caused $8,000 in damage and AirCover covered $2,100 after 3 months of back-and-forth. Now I use Safely (https://safely.com) per-reservation + Steadily (https://steadily.com) annual policy. Real insurance pays real claims. **6. I'd multi-platform from Day 1.** I was Airbnb-only for 2 years. Adding VRBO/Booking.com increased my bookings by 30%. I should have listed everywhere from the start. Read more hard-earned hosting lessons at https://strspecialist.com/blog.

Reply by Nolan Peters:

My biggest "start over" change: **I would not buy in my hometown.** I bought my first STR in my city because it was convenient. But local market ≠ best market. If I'd spend 2 weeks analyzing markets with AirDNA data, I would have found markets with 2x the revenue potential at the same purchase price. Your second biggest "start over" investment: start building an email list from Day 1. Using StayFi (https://stayfi.com) WiFi marketing, every guest's email gets captured automatically. After 2 years, you have 1,000+ emails of people who already loved your property. That's your direct booking engine — no Airbnb commissions on repeat guests.