Spent the last few weeks on my first ever board, a little passive sniffer that sits between two DB9 cables so you can watch the TX and RX lines with a scope. Sent the gerbers off, forgot about it for two weeks, and the boards showed up yesterday. Populated one tonight and it works on the first try, which honestly shocked me. The things I'd tell past me: give the connector footprints way more thought than I did. I copied pin hole spacing off a datasheet and still had to nudge the holes in the CAD model to get the plugs to seat without a fight. Also I put the test points in a really awkward spot right where the second connector hangs over, so my probe barely fits. Little stuff like that doesn't show up until you're actually holding it.
Biggest relief was that my crystal placement wasn't as bad as I feared, signal looks clean on the scope. One trace has a repair jumper under the IC because of a routing mistake I didn't catch until the boards arrived, but it passes the signal fine. Next revision will fix the footprint niggles and maybe add an LED so I can see traffic at a glance. Feels good to finally hold something I designed.