Does anyone have any clever solutions for getting two stranded wires into one hole?
Sure.
You can widen the hole with a small drill bit or a needle file.
You can also carefully solder the wires together first to make them more like a single solid wire.
Alternatively, you can solder the two wires onto the end of a single wire and cover the joint with heat shrink. Then, you are back to single wire in one hole.
I hope some of that helps.
Edit: I forgot a couple more tips.
You can drill a second hole.
You can carefully consider why (or whether) you actually need to solder two wires to the same place and consider soldering them to different places. ;)
Make the connection somewhere else.
What are you trying to hook up?
I'm building a Ludwig Phase II from Dead End FX... https://drive.google.com/file/d/18Z4xzPIDBDRFgt9jjflkUIS3L1WVR9m4/view
Holes 3 and 4 from the right on the filter board each have a wire that comes in and goes out the same hole. I think one of them is ground, so I could probably hook that wire to a different ground point.
Looking at that layout, I would just pair them up at the switch lugs instead of the second PCB. Make sure to tin the wires first so they feed through without fraying out. It should be pretty easy.
Thanks, everyone. I should be able to make one of these suggestions work.