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The other problem is, if an option expires, it sort of disappears from your brokerage account and you have to manipulate things manually after a download to quicken.

That part is as much a problem with your brokerage as with Quicken. It could be fixed on either end, if Quicken understood options. But I've had option positions expire, and my brokerage ( ) includes a transaction for the expiration - a purchase or sale (whichever is appropriate) at zero price with zero commission.
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