Yeah I've stayed at lot of airbnbs (20-30 a year) and only had good to great experiences. I've met a lot of hosts that I specifically look up when I visit their city again. I've had plenty where they weren't exactly what I expected, like thinking a cabin I was renting was in the woods from the pictures but it was on a gravel driveway with trees in the background, but my trip wasn't ruined or anything. I've unfortunately had reservations cancelled in the 24hr window and had to rush to find something else, or accepted an insta-reservation but never heard back from the host. I've not looked over the fine print, seen airbnbs with pictures of ovens and shown up to microwaves (this is my fault but the pictures don't help). Those are my biggest host issues.

I will say though that I dread what you said - analyzing listings. The airbnb.com UX is atrocious. I thought it was pretty sub-par when I'd look at listings just planning trips for myself. But now I try to plan trips with my partner through it and she has her own account, so I share lists and listings within lists. It's awful. I recently went on a 2 week road trip and stayed at different places every day. I'd have to have google maps open to plot distance between airbnbs and parks, I couldn't go back into a listings actual ad to see its details once I confirmed a reservation (I had to search for the listing again and go to it, the reservation details don't show the actual posting), I'd have to keep a separate app open just to keep notes of each listing, I use my todo list, which I then also had to share with my partner separately because there's not really a way to thumbs up/down/leave comments on listings. I'd send her listings and she'd get errors or they'd just never end up on her account. If I add her to a listing I don't think it shows up in her reservations so I still had to send all the info to her, she'd just get an email about it.

Does anyone do this sort of stuff on any of the other sites? Vrbo, etc? Is there a really good roadtrip planning app? Are they easier to use in these situations? I honestly don't want to deal with it again it was that frustrating.

Also, while I'm here ranting, and as an ex-airbnb host and very avid airbnb user. Please, chill out on your cleaning fees. I cannot believe some of the cleaning fees I find. Quit using it as a way to lower the daily cost so that you show up on more searches. Nothing turns me off from a place more than putting a reservation together and noticing that my 2-3 day stay will incur $150+ in cleaning fees. I would rather pay a slightly higher daily fee than $45-80/day in "cleaning" when I'm a single person renting your studio just so I can spend 80% of my day hiking outside of your place. I can't remember if I could control this based on the number of guests staying but if you can, please do it.