I'm not great at gifts but the thing I've learned is, consumables. Chocolate, wine, your bath bomb, fancy cookies, etc. They're fairly universal, won't run into the "already have it" problem, and don't leave the recipient feeling like they now need to hold onto something forever or risk offending you. You may not score a direct hit but generally if you know people at all you can't go too far wrong.
I used to make people cookies and sometimes candy. I'd try to have at least 4-5 varieties, individually wrapped at home, with rules: No nuts, no candy outside of chocolate chips, and most of the doughs would freeze well. I'd often include one new-to-me cookie, chocolate chips, snickerdoodles, brownies, and a colorful-but-plain sugar cookie.
They aren't fancy or anything, but they scale up well and folks will look forward to it.
I've made a bunch of fancy chocolate truffles more than once. The basic truffle can be rolled in all kinds of nuts and shit, so you get an assortment; the greatest expense is the packaging (pretty boxes, nice little paper shells to put them in).
Even if the recipient doesn't care for truffles (vegan, weight-loss dieter) they like the packaging, and they have something to share. And truffles are easy to make.
For a few years now we've bought a bunch of peaches sometime in the summer and made a bunch of peach jam, put it in pretty little jars, and brought them to holiday gatherings with my family around Philadelphia. It's always a hit.
The thing is, they actually have good peaches up there too! I know this because I ate so many of them when I lived near a good farmer's market there!
Ah, Gram Parsons, the "Georgia Peach". And Duane Allman.
Philly peaches: I believe that Robert E. Lee's troops got through a lot of "foraged" (stolen) peaches on the march to Gettysburg. Presumably squits was a big problem in the confederate army.
My family pact this year is we have agreed to buy each other stationery. Paper, pencils, stickies, and fountain pen ink — all consumable and easy to find something for everyone (especially if they like sushi, cats, or owls.)
