^That's good to know, for weird footprints in X and Y directions. It seems like the obvious way to do it. But I've only ever seen people stick the pins in a drilled block of MDF or plastic or whatnot. Not only just online, I've worked with other PCB designer who did it for simple SIL interface.* I've never had need for a complex pogo pin footprint; it's good to know it's as simple as this.
The sideways method works fine for SIL interface. In over a decade, I have never broken one of these. Used in CNC machines, arbor presses, by hand, 10's of thousands of repetitions. This is ideal for a hand-held interface, because of the streamlined shape.
It doesn't take a lot of force to depress a pogo pin. Not only I have never pulled a pin/pad off the interface, I've never had to replace a single pin due to damage or wear, at least not since upgrading from the cheapest pogo pins.
*He actually outsourced these jobs, and this is what he received. His interfaces were machined some kind of resin cured MDF or something, drilled for the pins, and hand soldered flywires to a header. The custom arbor presses he provided our shared client was also made of the same material. They looked more or less exactly what you can buy on eBay for this task, if you search for testing jigs/arbor press. This is common enough there are apparently companies that make this stuff to order. I never cared to ask where he got any of this stuff made, because it was all over-complicated and stupid. OTOH, he asked a lot of questions and requested way to replicated a lot of my equipment, mostly diy and off the shelf stuff, easily adaptable/adjustable to different jobs.
He wasn't too much of an engineer; mostly a businessman. He employed one high school grad across the country to do the PCB design, and he paid for the Altium license.
CNC machining/drilling probably makes sense for a business that makes custom jigs, for minimal cost and turnaround time vs ordering one-off PCB.
Edit: NorthGuy, I see from another thread, you tend to use plated thru holes in random layout for your pogo connections, and using low density, large diameter pins. The advantage of using pogo pins is you don't need thru holes. This alone negates much of the space advantage of random pad placement. And using a standardized footprint means you don't have to make new hardware interface for each project. I have used same footprint and interface for a variety of projects, and in one case I saved space by mixing up the pinout to cram it in there. Then just rewire the interface pen using the jumperpads I put there for that purpose.
If you might ever need to support/maintain past projects, you will also end up with a collection of these large, bulky interfaces.
And FYI, the teensy 0.05" pins are rock solid, if you buy the good ones.