Is your mechanic a VW specialist? If not then its probably worth taking it to an independent VW specialist mechanic to have the transmission diagnosed. Otherwise you may well be signing up to spend thousands of dollars unnecessarily.
But if there is something terminal with the gearbox, then you would want to know about it so you can plan what to do. Personally I could never trade/sell a car with a fault of any kind without disclosing it to the buyer and pricing the car accordingly - but people do this every day and then some poor unsuspecting person buys a ticking timebomb.
Assuming this is the notorious 7 speed DSG and you have a 1.2TSI or 1.4TSI Golf, then I don't think its worth the investment to overhaul the transmission - as this will almost certainly cost more than your car is worth. Which leaves either diagnosing the issue(s) and replacing those specific parts, or buying a used DSG from a wreckers and having that fitted.
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