I'm currently on my second Airstream, and overall, I've had a good experience. I like the classic design of Airstream trailers. Their layouts are functional, and they tow quite well. I had a Raptor Toy Hauler before so that's what I'm comparing it to. My in-laws also have a 2008 Flying Cloud 25FB and they've had very little trouble with it.
You can usually find a good deal on Airstreams that are 2-3 years old. I first bought a 2014 Flying Cloud 27FB in 2016. After enjoying it for seven years, I sold it for nearly the purchase price. I never had any major issues with it other then tires! I finally switched to Goodyear Endurance tires and haven't had a problem since. (knock on wood!)
Earlier in the year we found an awesome deal on a 2020 Flying Cloud 28RB that was down in Buda. This floor plan seems to suit our family better now that my kids are older. I also went with a dual AC setup to hopefully extend our camping season a little longer. The new AC units are really quiet and do well cooling down the trailer.
There is a checklist on AirForums that is worth going over:
https://www.airforums.com/forums/f138/trailer-inspection-checklist-43294.html
There isn't much ground clearance, so I've had problems scraping the rear end of the trailer. I'm planning on lifting it 3" and possibly upgrading to 16" wheels & tires next year. I think that will give me a little more confidence for longer trips.
Let me know if you have any other questions!