I've struggled with appropriate wire-to-board connections over the years.
Here's one of OMSI's mainstays that I've co-opted that I'd like to share:
all you do is
Step 1: add a hole in your printed circuit board
Step 2: route the wire through the hole
Step 3: solder the wire to the board
in this case its a 22 gauge wire, 0.1" through hole for strain relief, and a 18 gauge pin hole to solder to.
Wire is strain releived at the board. Connector is off the board
Shift registers for 64 inputs/outputs and their wires.