Pretty good progress over the weekend working around kids and household obligations. It's not the picture perfect dovetail joint you see from people who do this sort of thing on the regular (looking at you Frank Strazza) but for my first go of it I'm really pleased. I took my sweet time finessing the fit of the tails to the pins on the end cap such that it is nice and snug, not loose, not so tight that I have to pound it in. I can get it seated 90% just by pressing down on it with my upper body weight and driving it home with a few light taps of a rubber hammer.
I didn't invent this idea of doing the pins. It's from Jameel Abraham (of Benchcrafted). He wrote up an article about a decade ago in Popular Woodworking detailing it. It's also featured on TWW build video. Once you have your tails square and are happy with everything you transfer the knife lines to the pin board and very, very carefully chisel and rout out the first 1/4" so you can rout the remaining depth with a pattern bit and a router. I hogged out the majority of the waste with my 1400 and a guide bushing and a 1/2" spiral upcut and proceeded to do the final passes with my little dewalt cordless trim router with the pattern bit. After that was done I had to do some investigating with a pencil to find what was holding it up. Just mark up the tail sides all over and look for rub marks and address the proud areas of the pins with a sharp chisel.
End cap trimmed proud so I can plane it flush after glue up:

I scribed the tails directly to the walnut endcap, then placed tape away from the knife lines and found them again with my fingernail. Reason for this is the first 1/4" gets routed out free hand close to the lines before the chisel. Having the tape was a great visual indicator of when I was getting close enough to stop.






There's about a 1mm gap at the top of the bench between that tail board and the end cap where my knife line didn't meet up perfectly when I wrapped it around. I've already worked out how I'll cut a piece off on the table saw to glue in there after I finish flattening the bench. Otherwise very happy with everything so far. The tails were cut entirely by hand and are my first dovetails of any kind.
Matt