Hello, I have a kind of stupid question but i really need an answer, so i have a Vintage VS6 guitar which I bought used from my friend whom bought it from some other guy long time ago and i have cleaned it quite a few times and once i changed the tunning pegs to some cheaper ones because those looked used too much. Basicly the new ones were even bigger shit and after changing back to old ones i noticed that the holes where the screw should go look really ****ed and the screw doesn't go into them as good as it used to. Thats the backstory now the main question it's still messed up like this but im considering to go from 009 string gauge to 011 for more sustain and might the tension cause to break the tunning pegs or even mess up the headstock even more?
If the screw holes have stripped out so that the screws don't hold any more, just drop a short piece of toothpick (or other wood splinter) with a touch of glue into the holes. Going to 11s shouldn't be a problem.
Exactly. I don't think I have a guitar with a screw somewhere that does not have a toothpick plug...For larger screws match sticks work better. Let it sit overnight so the glue can cure before you use it.
Hmmm...I wonder what this button does...
^^^^ Me too. Just about every time I do a mod it involves toothpicks (actually bamboo ske wers in my case). I did one just yesterday the has now been plugged and redrilled at least four times.

When doing small screw holes I glue the plugs in then drill pilot holes with a small drill bit held in an hobby knife handle. You can get them in without the pilot hole, but the pressure can burr or strip the slot on cheap screws.