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“Do people drill into Classical guitars? I have a Classical guitar and would like to have strap buttons installed for a guitar strap.”
Well, before you even consider drilling… know that there are “Classical” guitar straps available. Don’t be fooled by the name though–they’re not just for Classical guitars, and work great with steel string acoustic as well. They’re physically different than the usual 2-button guitar straps. Willie Nelson uses one with the old, beat-up Classical guitar he plays. Here are 3 that I really like:
Now, a word of caution: with a Classical strap you can’t let go of the guitar with both hands–at any time. One hand must be on the guitar at all times or the guitar will flip out of the strap whenever you’re standing. The upside is that it’s really quick/easy to attach and remove the guitar. Pick it up and hook it underneath. When your done, simply unhook it. You just have to be aware and NOT take both hands off at the same time.
Now, to answer your original question about drilling…
The drilling question really comes down to how nice the guitar is. If it’s cheaper and/or you aren’t concerned about devaluing it, you can definitely have a guitar tech drill a couple strap button holes. I’d never do this to a good Classical guitar, but I wouldn’t hesitate to do it to a cheapo one. You just have to make sure it’ll balance right first. In other words, you might drill holes and install strap buttons only to find that it “neck dives” because the center of gravity is off and the neck + headstock keep heading toward the floor. You definitely don’t want that.