Aftermarket cooler definitely
isn't mandatory. As far as you watch your temperatures while stress testing there's nothing wrong with trying. You should actually be able to quite confortably overclock to 2.8-3.0GHz region with stock cooler. You won't obviously be as effective with stock as you'd with aftermarket cooler but there should still be some headroom above the stock speeds.
I'd try that 7.5 x 374 again with adjusted voltage, something like 1.3 volts to start with. If it still fails you can try upping it by 0.025 increaments (1.325 -> 1.35 -> 1.375..etc) all the way up to 1.4 area which is still considered safe (if you feel like pushing it, 1.45 is the absolute maximum I'd risk).
If for some reason that still doesn't boot start reducing the FSB. Controversially, if it works you can up the FSB as long as you stress test between tries and watch the temperatures (75-80 degress during prime 95 would still be reasonable, if it goes above 85-90 I'd definitely abort and reduce either volts or FSB).
You can try to fine tune by reducing RAM speed and/or losen the timings. For more tips and settings to fiddle with try to google "Intel core 2 quad Q8300 overclocking guide), should always yield some additional info.
Good luck and make sure to post results!