I'm in a similar situation, and just dropped of my sled to have some work done. Here is what I have found via internet and recommended by mechanics. Mechanics that work on all the different brands know what to look for in terms of wear and tear depending on the make/model of sled.
I have a 05 Skidoo Renedgade 600HO with over 7000 miles. I am the original owner. It is very clean, still looks new and is my back up sled that I wish to keep going for a while. Maintenance I've completed over the course of the years: new/rebuild shocks throughout (amazing difference). Lube entire chassis, including drive shaft bearing zirk fitting by speedo multiple times a season, clean exhaust valves/power valves every season, new carb boots and reed valves (common issue for SD), primary clutch rebuild, including new spring. Every season for storage, I put stabil in the gas, run it through the motor, pull plugs, carbs, reed valves and soak internal components of motor (pistions, rings, down into the crank) with storage fluid. Clean the carbs and drain the gas out of the float bowls.
Things I am having done as "preventative" by my mechanic this year:
new top end rebuild (if necessary- even though I have good compression, I figure I am on borrowed time with a 2-stroke). Depending on wear, he may just do new rings, otherwise will do new pistons and rings.
pull drive shaft, inspect drive train, check for slop, replace bearings.
rebuild rear shocks again (has 3 years since last rebuild)
you really can't do much "preventative" for the crank, when it goes, it goes. The 600's hold up well during that year, however he has rebuilt a lot of the 800's in that same year, so that's what I mean by trusting your mechanic to know what to look for.
Hope that helps a little....