I'm fortunate that I do have a trusted friend in NJ who I've been travelling with since the 60's and may be coming along with us if our dates fit with his business commitments. We did a big Wing tour (early GL1000 Wings) together back.... hmm, must have been at least one wife ago each. How time flies.
Buying an older good condition Wing is more or less what we'd planned to do. Once we've got the dates sorted out I'll probably just send him a load of dollars (or if the pound does its usual trick, a few dollars) and trust his judgement. After all he'll have to help push if things go wrong.
We'll just reverse the procedure at the end - leave it with him to sell as and when after our return. Leaving it there for future trips is something we've thought about but probably won't make a decision on until somewhere near the end. You never know, if things take their usual turn I might need the money for another divorce settlement
Where to find something suitable is an interesting question. There does seem to be a number of them on ebay but spread all over the country and it's unrealistic to ask John to check out a bike in Nevada or Louisiana or somewhere equally remote from the east coast. Wing forums isn't somewhere I'd thought of and is certainly an avenue worth checking out.
Style (life-style more likely) wise they're not really me and I've had no desire to own a modern one in the UK but if we're going to do this you have to put some effort in. If I was going on my own I'd probably just borrow John's KLR but I can't see my other half spending a month on the back of that. If we're going to have to go the big lardy tourer route then why not go as big and lardy as they come.
Pic from back in the days when I thought these were big -
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