I think limited installation DRM has probably caused problems for serious gamers at least once, if it was a game they actually enjoyed. Limiting your installs to as low as 3 times for a game you love is absurd.
Additionally, I know games that require an online activation have resulted in serious frustration for me several times, because the publisher's servers inevitably can't handle the Day-1 traffic.
Ignoring those types, though, I remember when my copy of Operation Flashpoint: Dragon Rising arrived, the DRM (SecuROM, if I recall correctly) wouldn't recognise my dvd drive. I don't know if it was too old or something, but it just flat out refused to install the game. I could get onto the auto-play splash screen, but as soon as I clicked on anything SecuROM popped up with an error about my dvd drive. I know I wasn't alone with this problem.
After a few days of frustration and useless tech support, I simply pirated the game I'd paid for in order to be able to play it. These days I just won't buy games with brutal DRM. Steam's is about the only kind I can stand.