Having sausage-like fingers myself I'd agree that bigger is better, but...
Just because there is a screwdriver slot there's no reason to go mad tightening up the screws.
Over-tightening D-Sub screws can cause problems:
- Stripping the tiny M3 threads. Sometimes they lock and won't come out, sometimes spin and won't come out. Either way it's a pain when they won't come out.
- Tighten so hard that the thread locks and when you undo it the nut/screw from the plug/socket in the case comes out with it. Both going that way can cause you to lose the connector inside the case (depending on whether it is a circuit board mounted one).
- Tighten so hard the connector is graunched off the circuit board inside the case (see previous 'depends').
- End of the screw snaps off.
- Captive nut on the unit snaps off.
- And combinations of the above.
Been using computers (PC's, minis, mainframes, embedded systems for manufacturing) all my working life. Seen all the above and more besides.
Doing the screws up just snug is perfectly adequate. The weight / tension / twist of the cables will pretty well always ensure there's sufficient friction on the threads that they won't come undone.