IMac startup gets stuck on grey screen

This is an intermittent issue and has only been happening for the last week or so. When I start up my iMac (bought early 2008, running Snow Leopard and fully updated) it will get stuck on the grey screen before the apple logo appears.
I have to hold the power button for a few seconds to shut everything down completely and turn it back on. Second time round it seems to power up fine (so far) so I'm a bit bemused as to what the issue is. I keep my external HD plugged in, so that's always connected when I boot up, but that hasn't been an issue before...
I've been having the issue since I bought my iMac back to uni. I'm always careful to package it properly (back in its original box) but I guess maybe it got clunked in the car? I don't know whether that would have an impact or not. I'm also careful to keep around 100Gb free on my HD to keep it running smoothly.
Any ideas would be hugely appreciated, as final year of uni is not a great time for my Mac to break!

OK, yes 100GB out of 320GB is plenty of space, the rule of thumb on Macs is you should have 10-15% of HD space available.
Regarding your power, that's a possible cause. If it does prove to be the problem I would recommend investing in a battery backup to ensure your iMac is not only is getting consistent power but is protected in the event of power failures or power spikes.
There are some things you can check, although they aren't 100% definitive they can give some clues. First is open Disk Utility (Applications-Utilities-Disk Utility) and check the S.M.A.R.T. status of your internal HD. It should say Verified, if it doesn't it's definitely in trouble and either needs repairing or replacing. You can also run Repair Disk Permissions in Disk Utility. Both actions should take less than 10 minutes on your machine.

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