Hi skistream 54. This forum has been invaluable to poke around in and get most of my questions answered. The search function really helps.
I am in Portland and currently I am having a '58 Overlander remodeled inside that I just purchased this past summer. I started out looking at everything in years and models on the internet. blogs, ebay, craigslist, threads on this forum. I poured through it all. I narrowed it down to an older trailer due to my ballpark budget and then I looked at everything I could find on older Airstreams. I went with the 58 because I love the body style, I am charmed by the vintage feel and the history and the better grade aluminum. I also wanted a trailer that had spent its life in the desert vs some wet mossy PacificNW woods.
You might like something newer. But the process is the same. Start looking and thinking and reading and you will start to get a feel for what you want.
I started out looking at mid 70's models but they didn't do it for me. It just kind of went along a path that got narrower the more I studied and shopped around until I felt clear about what I wanted.
I didn't want to get involved in handson nuts and bolts restoring ourselves as I knew it would go very slowly and I wanted to use the thing in my lifetime. (some people are better disciplined with their productive time than we are) I bought one that had the running gear, hitch leaks, and most electrics replaced. It had been polished and was in relatively beautiful shape. It just needed the interior made pretty and renewed.
So I think it really depends on what you like. If you like things that are modern and can afford the newer, you may find yourself heading in that direction. I also looked at models that had some restoration done to them and could be taken out on the road immediately, but I knew I would still want to remodel to my own taste.
I have my Overlander at RVPro in Vancouver and they are doing a good job and keeping in good communication and are being conscious of my budget. I had tried a couple of other places, but one wasn't enthusiastic, and the other didn't really like to work on trailers in the winter. so thanks to this forum and some good comments on RV Pro I went there and so far have been pleased.
I will have about $21k into the trailer by the time we are done including the purchase price. Then anything else (and there is always something else) I will have done at a more leisurely pace.