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Rookie strap lock question

What unknowns am I facing when replacing the original strap buttons on a 1970s Carvin bass guitar with a modern day strap locking set? Clearly am not wanting to do the wrong thing here.

Fearing that it is not as easy as unscrewing the old and replacing with new in the same holes. Righty-tighty, lefty-loosie is close to my level of carpentry skill.

Suggestions, size concerns (drilling?), brand names, pitfalls to avoid, technique assistance would all be greatly appreciated by this member. A brand new Levy strap did not hold the instrument securely at the top (button seems relatively tiny) and this instrument is too valuable to take a header.
 
Schaller and Dunlop strap locks are go-to for most. I personally really like Ernie Ball super locks, they have a smaller profile and keep your strap closer to the instrument, there's not much potruding going on. I also like how on Ernie Ball locks you have to press two buttons to detach the strap locks so its practically impossible to accidentally unhook the strap. I also like the looks of them and haven't had a single incident in the 5 years of using them so far, just make it a habit to give it a quick tug check on both ends as you attach the strap, regardless of what strap locks you end up using.

Lots of people like using the original screw as long as it fits the strap locks, that being said it might be wise to use a new screw with a bass that is 50 years old, screw material degradation and whatnot. Common way is breaking a toothpick into small chunks and filling the screw hole, adding a bit of glue, then screwing the new screw into it as it digs into the picks, and letting the glue dry. This works well if you have a screwdriver that has a healthy tip and you do it right. Otherwise a potential pitfall is that near the end as it gets tighter (it's normal) your screwdriver strips the screw and then you can neither screw it all the way in, nor unscrew it.

Alternatively you can just fill the hole with toothpicks and glue and let it dry, then drill a new hole and simply screw in the button. Some people are uncomfortable with drilling and that's understandable.
 
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I've got Dunlops on both my basses. They use a screw diameter that's larger than the stock Squier screws, so it was a case of drilling, not filling. The instructions tell you what size bit to use (can't recall off the top of my head).

Some tips:
  • Place the drill bit next to the new screw so that the tip of the bit is touching the underside of the screw head. Then, note where the pointy end of the screw lines up on the drill bit. Wrap a piece of tape around the bit at that point. That's your depth guide.
  • Make sure (as dax12 said above) that your screwdriver tip is the proper fit for the screw to prevent stripping out the head.
  • Rub some wax (candle, chapstick, or some such) on the threads of the screw to make it easier to screw in.
For me, the more difficult part of the installation was putting the clasps on my strap. Took a fair amount of pressure and a pair of needle-nosed pliers to get the C-clip securely into place. Thickness of the strap will play a role there.

So far, so good with the Dunlops.
 
When I replaced the pins on my 20 year old Carvin, One of the screws would not tighten properly again.
I took a slightly lager screw, a tooth pick and a bit of wood glue. Coated the tooth pick in glue, put it in the hole and snapped it off, then put in the screw. Maybe not the most elegant solution, but it worked.
 
I'll throw this out there. Instead of replacing all my strap pins with strap locks I just use Grolsch beer gaskets. They're the same thing Fender and Dunlop sell for like a dollar a piece, except you can get a 100 pack for like $12, or better yet buy a pack of Grolsch and get strap locks and beer. You just put the strap on the current pin, and then slip the gasket over the head of the pin.

https://www.amazon.com/Naruekrit-OT...t=&hvlocphy=9031138&hvtargid=pla-554592002350
 
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