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I know if I transfer it into his name, if he doesn't sell it, I will have to keep track of the old cost basis for him going forward, which isn't practical.

Why would you have to keep track of it? Give him a copy of what Quicken says the basis of the stock is as of the date he's taken over the account, and then wash your hands of it. He can decide if he wants to keep reinvesting dividends (which I presume is the biggest concern you have, since the past basis already is determined) or get them in cash, and he can decide if he wants to sell.

Is it worth me bothering to transfer it into his name, only to have him sell it in his name?
Or could I sell it and just include the gains in his tax return, as we have been doing with the dividends?

Assuming he's actually reached the age of majority per your state law (they aren't always 18 or 21), I would suggest that you not take any actions on his behalf, other than starting and signing paperwork to transfer the account to him.

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