Hi there,
Yes they do,(drill them thru) the pogo’s will depend on the thickness of the socket.
the right angle (bent headers) overlap and touch the tops of the straight set.
It’s a WIP, so the dimensions have change slightly , mostly to make it skinnier and thinner and a notch in the rear for room for the Antenna on the ESP series chips. Also adding the connections to the battery pads on the bottom so REV3 is on the drawing board.
Pogo’s come in basically two styles, Flat bottom and Board mount.
sizes this one is 8.75mm (I recommend get a few bigger and smaller) they only cost a couple bucs, but the shipping is more, LOL so wait and order a few things to make it worth the freight IMO.
HTH
GL
PJ 
Time is tight these days, I’ll tweak and upload a fresh model to thingiverse with aforementioned enhancements asap. 