I have a 1990 Polaris 500 Classic. I have no clue when the chain case oil was changed or even inspected last. Is it easiest to just tip the sled on its side and pull the case cover? Not sure if there is a drain plug somewhere.
DT
That’s right around the time they started putting dip-sticks in the machines with magnets to collect the metal shavings. My 91 POPO had one not sure about the 90 you have. Newer Machines have an actuall drain plug making it easier yet …..if you have the dipstick you could suction it out if you have acces to to a pump…. BUT at that age it might be a good idea to just pull the cover and inspect the gears and chain. Look for cracks or chips in the chain and gears. Check the tension.
Good luck!
Seems like all my Polaris’s had drain plugs. I know my current one’s do but they are newer. Obviously check for that directly underneath. It would likely be flush and require an alan wrench. With sled that old the best idea woul be to pull the cover so you can inspect and clean well. You’ll likely have to pull the exhaust which is no big deal. I would just get a new gasket. You may be able to reuse the old one but somehthing that old who knows.
Put absorbant rag in bottom of belly pan and, remove chain case cover and inspect the chain tensioner. It is probably a nylon part that may need to be replaced. I think the cover should have a large o-ring rope seal i think. Should hold one pint chain case lube. Easy job. Will take three beers to do. 
Not sure on your particular model, but there could be a bolt that is a chain case drain plug on the inside of the tunnel. It can be tough to see, but it’s located directly behind the chain case and inside the tunnel.
Otherwise, (like already mentioned) rags stuffed below the case will do it. It can be messy.
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