I used to experience condom breakage once a year until I figured out the common factors, now it's I think once in last 5 years and that was for one particular reason that I can prevent or eliminate in future.
Interestingly studies of condom failures have noted that increased experience by users leads to a significant reduction in failures.
Whilst this thread is entitled 'breakages' there are other reasons for failure including slippage which is distinct from breaking, although slippage may also result in a ruptured condom.
Everything seems to have been covered by others, but the broken condom rate is judged at less than 1% if all other parameters are met in terms of correct use. As a result condoms are considered to be around 98% effective for pregnancy, but in practice, due to all the possible misuse factors, this can drop to below 90% quite easily and potentially much lower in extreme cases.
As has been mentioned in the past punting is atypical in that in most instances the female applies the condom rather than the male and many SP do not use a roll on technique.
I have had very few condom breakages in my lifetime, but did have two in one paid for session which the SP blamed on the condoms being used in the parlour, as it had happened to her on other occasions. All was well though.
Finally remember condoms should be used for a maximum of 30 minutes before changing and my own view is that timescale should be reduced depending on the type of sexual activity. Lube is so important too.