Hi there

I ran in the Skye Games last year. The race is not too hard (except for the last couple of hundred metres on the way up, first couple of hundred on the way down).
No need to take any special gear.
Hill running shoes essential if you want to be competitive.
I was 10 seconds behind the leader at the top and on the way down lost a minute because I could get no grip.
(Incidentally, the guy who won it was a Scottish champion).
The rule, like BoabyBoy said is, get to the flag and back... that's about it :d
The best route is: (if you prefer the excitement of searching for the best one for yourself don't read this paragraph) - out the track, onto the tarmac road, to the left, onto the graveyard, cross the graveyard onto the bay, cross the bay (if tide is high watch out for the deeper, slippery bit nearer the games grounds), aim for the petrol station, keep to the right of it into a drive, when the track forks take left - then just follow the fence up the hill. Trace your steps on the way back.
It's a short race, I would say the difficulty level is quite low. Makes an exciting change because most races are very strenuous. This is fast, you must keep your brain working all the time and the terrain is as varied as you can get: grass track, tarmac, rocks, sea water, fresh water, a graveyard!, heather, mud and the occasional pile of... hmmm... dung
The atmosphere at these games is fantastic.
You will be charged a fair amount (£8 last year) to get in. Tell them you are a competitor and you will get in for free.
If someone insists you pay, tell them to get someone else. Participants don't pay despite what some may say.
And have fun
