I'm largely the same, jags, though I do like my bargains. I just laid-in three NOS closeout examples of my favorite helmet for USD$23 each instead of buying one from current stock that doesn't fit as well and paying USD$130.
Yes, you really take care of your things -- I've seen them in photos, looking as-new. Your bikes, too.
From here across the Pond, I always look at even the highest of used Thorn prices with amazement. They all look like bargains until I figure in the exchange rate and overseas shipping and customs and the lack of Thorn's brand-new components, setup, and golden warranty.
Used bikes tend to be a real iffy purchase here, especially if one can't see them in person. No matter how good the paint and external condition are, the bearings are almost always shot, dry, worn-out and in need of a replacement. Surest bet is to buy a used frame, but then alignment and tracking can be hard to judge.
I keep my old bikes (mostly from 1970, 1972, 1977, 1980, 1984, 1989) out of sentimentality...and because I realize they'd never bring what they're worth to me. On balance, for the joy they still provide, it's better for me to keep 'em and ride 'em.
Best,
Dan.