Turnaround
Commercial User
Longer is not the answer either. Let's say the original screw went 1" deep into the wood, but it got stripped. So you put in a 1-1/2" screw. The original screw had 1" of thread holding it, but now it will have only 1/2" of thread holding - the first 1" is already stripped., So that screw will strip more easily and when it does you put in a 2" screw, which will only be holding on the last 1/2" since the rest is stripped. Repeat with a 2-1/2" screw. and on an on until the screw comes out the back side of the bass at which point you replace the screw with a long bolt with a lock washer and nut on the butt end.Longer yes, the diameter need to remain the same.
Cram some glue covered toothpicks into the hole.
Screw the strap pin in while glue is still wet, let it setup for a day.
The problem is actually that the screw is going into the end grain of the wood. That strips fairly easily whereas screws going into the cross grain will hold much better without stripping. So both toothpicvks and dowels alone will not provide a more secure fitting - they buth provide end grain relative to the wood screw. But if you use glue on the toothpicks it will improve the situation a lot. Here's why.
This pic represents a screw going into the end grain of the wood. The fibres run parallel to the screw and you can see that the red fibres are severed by the screw threads into small pieces - for clarity I show large fibres. These chopped up fibres have little strength because their bond to the neighbouring fibre (yellow) has be broken for much of their length, The bond is reduced by about 50% and thus holding strength is likewise reduced.
Compare that to the the screw going into edge grain. Instead of the screw being held by a fibre that has been severed into small pieces, the screw is held by many fibres that retain their bond with their neighbours.
When dealing with a strap button, the screw will be going into end-grain of the wood, so the best approach to avoid further stripping is to reinforce the bond between the fibres. Glue is made for just that purpose. So toothpick coated with glue are a good solution. Another solution is to bore out the stripped hole and glue in a cross-grain plug - not a dowel which would only present end grain to the screw.