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Anybody make a small claim before?

Best case - you get a judgement and no way to force them to pay it
Worst case - you lose and they have legal docs to tell you to get bent

I would go over the sales guy's head and see if his manager/club pres will do anything. There is no proof that it wasn't full at the time of sale or that something you did caused the issue. Plus they likely can point to something in the official docs or state boating guidelines that the captain/owner/driver should always check all fluids before starting engine or putting it in the water, especially at start of season. Then they can say they will give you the oil as a compromise but the damage due to your negligence is on you.

In a court there are a lot of ways this could turn out bad for you. Going over the sales guy would be step #1, then social media badmouthing - but make sure its all factual or they can get the reviews pulled.
 
My guys didn't fill the transfer case on an $100k Excursion that I sent to Norway. :mad3:
That one cost me.
 
Too much time has passed. If you or anyone else had a sustomer/private buyer claiming damage 4 months later you'd tell them to pound sand as there is no way to tell what happen between then and now. If it was the next day, week... that would be different.
 
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