How to make a GDB breakpoint only break after the point is reached a given number times?

Read section 5.1.6 of the GDB manual. What you have to do is first set a breakpoint, then set an 'ignore count' for that breakpoint number, e.g. ignore 23 1000.

If you don't know how many times to ignore the breakpoint, and don't want to count manually, the following may help:

  ignore 23 1000000   # set ignore count very high.

  run                 # the program will SIGSEGV before reaching the ignore count.
                      # Once it stops with SIGSEGV:

  info break 23       # tells you how many times the breakpoint has been hit, 
                      # which is exactly the count you want

continue <n>

This is a convenient method that skips the last hit breakpoint n - 1 times (and therefore stops at the n-th hit):

main.c

#include <stdio.h>

int main(void) {
    int i = 0;
    while (1) {
        i++; /* Line 6 */
        printf("%d\n", i);
    }
}

Usage:

gdb -n -q main.out

GDB session:

Reading symbols from main.out...done.
(gdb) start
Temporary breakpoint 1 at 0x6a8: file main.c, line 4.
Starting program: /home/ciro/bak/git/cpp-cheat/gdb/main.out

Temporary breakpoint 1, main () at main.c:4
4           int i = 0;
(gdb) b 6
Breakpoint 2 at 0x5555555546af: file main.c, line 6.
(gdb) c
Continuing.

Breakpoint 2, main () at main.c:6
6               i++; /* Line 6 */
(gdb) c 5
Will ignore next 4 crossings of breakpoint 2.  Continuing.
1
2
3
4
5

Breakpoint 2, main () at main.c:6
6               i++; /* Line 6 */
(gdb) p i
$1 = 5
(gdb)
(gdb) help c
Continue program being debugged, after signal or breakpoint.
Usage: continue [N]
If proceeding from breakpoint, a number N may be used as an argument,
which means to set the ignore count of that breakpoint to N - 1 (so that
the breakpoint won't break until the Nth time it is reached).