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I play around 3 times a week for 3-5 hours each time. On average I probably break strings twice every three weeks or so when I'm playing at that clip.
If the grommet is the cause, just replace them, or get some string tubing to use in that spot. The tubing is a little easier to deal with, so that's what I use:
I'm not sure of a time frame of my strings breaking, because I've never timed it. But it seems like I'm always restringing my stuff. Thinking about getting a few more racquets just so I don't have to restring them immediately.
Normally I can get 5-6 sets out of a 15L gauge, and probably 3-5 sets with 16. I won't even use 17g anymore. I'd end up spending more time stringing than actually playing.
I've played 3 sets on my newest 15L prince topspin job, so I'm guessing it'll probably break at some point in the next match. Broke a string yesterday with the 15L, and I think it was the 2nd or 3rd match I'd played with that racquet.