Hello from Colorado. Heck, you could travel around New England for 10 summers and still find something new and interesting. I love your home state and the area in general.
I too was impressed with how Airstreams are built. I too recommend a used trailer as you avoid the depreciation curve of a new one. We travel in a 86 Limited 34' and I'm working on a 75 Overlander 27'. Both of these trailers are in good shape.
These Air Forums have a list of folks who are willing to inspect a trailer for you. They use a checklist of all the structure and systems on the trailer and report back on strengths and needs. For example, body and frame in good shape, furnace doesn't light, subfloor has soft spot by the door, tires need replacing, cabinets in good shape. The inspection is just the facts, no marketing fluff. Inspectors don't care if the seller says it is "perfect" and "beautiful". You can find these inspectors on Air Forums / "portal page" (1st tab on the top left) / then about half way down on the right side of the portal page. Fill out the request form and see who might respond. If you see a trailer in the Denver area, I would be willing to inspect it for you at no charge.
I think the nineties trailers are pretty solid. I think the mid-aughts trailers may have some rear floor rot problems due to a poor rear body to bumper seal, and some frame issues that I would check out carefully. I think the trailers past 2010 are also pretty solid. Older trailers like mine have problems develop due to age. Older trailers will take more maintenance and repairs. I enjoy working on my Airstream.
I think these Air Forums will be very useful to you in your used Airstream search and much additional information.
David
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WBCCI #8607 VAC Region 11
KnowledgeBase trailer renovation threads: 69 Globetrotter, 76 Sovereign, 75 Overlander, 66 Trade Wind Such fun !
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