You can ALWAYS find a deal in Vegas. The wild card is airfare. I've had a lot of luck with Southwest lately but you know how all that works.
WIth regard to season, seems like late summer (August) wasn't too bad. It was hot as all dickens tho. Guess that's probably why. But at any rate, it wasn't hard to find a cheap flight and got a good room rate.
Make sure you go Monday thru Thursday, you get much cheaper bookings, or much nicer hotels for your budget.
Go to the LA Times web site, check the print ads to see who is running specials. Also, check Travelaxe.com, a super way to scan the internet for specials.
Consider some of the downtown venues. Main Street Station is a nice joint and it can be really cheap. (Watch out for the fake two-deck tho). The Golden Nugget is a 4-star resort, and its usually not cheap but sometimes they run specials. (They have an excellent deal going now).
My wife thinks the best value on the strip is the Mirage. Their rooms run about a third of what Bellagio charges but it is a really really nice place, very plush and very classy. Don't look for much in the way of comps, but especially if you go early in the week, the rent shouldnt be too bad, and it will spoil you so much you might feel guilty.