Here's to wishing I was in the tri-state area and we could just hang out on occasion.
Feeling super alive and vigorous so I wanted to contribute my 2 cents: I've had similar experiences, but I arrived at a slightly different decision.
I essentially gave up on tracking. The extra expense and post office hassle hasn't brought me any additional peace of mind, or help, at least as far as Deckbox is concerned. Sketchy people are going to be sketchy, regardless. And I've tried all manner of approaches with it, like tracking without the person even knowing ("aw, man you didn't tell me it was arriving today, I guess someone stole it because now it is gone") or making a big deal out of the process with visuals of each step. I just avoid tracking now and trade (as cheaply as humanly possible) with the folks I trust 100%. It limits my pool, sure, but the trading process is cheaper and breezier, and regrets are minimized, thanks largely to folks like Steven and this group.
YMMV, so this is just a working theory for now, but if you can find the little fuckers (most post offices in Seattle do NOT have them) you can send heavier envelopes just under 2 oz with the extra 1 ounce stamp (a meager 20 cents) which has been a real life saver, as far as having things delivered successfully. Knock on wood. The mail carriers seem to give those extra attention, for whatever reason (vs. 2 or more forever stamps, which let's face it, is soooo uncool and deserves to get tossed in the garbage).
Happy to read other people's workarounds and epiphanies as well.
