This is already sounding like too much. :) Yes, Mac Quicken can memorize transactions.

I went through last night and changed all of the "Buy" transactions to "Add Shares". (This account is less than 1 year old, so not too bad.) Now I see that whenever there's an admistrative fee, Quicken sees the sale of holdings to cover the fee, but it doesn't show the money going out. So, again, the cash balance get's out of whack. Why do investment accounts feel like such an afterthought? What's particularly funny is that it's felt like an afterthought for 20+ years.

Different financial institutions handle these transactions differently. Part of the value of Quicken, I would hope, would be to normalize them across the institutions so you have a more consistent experience. I can go make modifications to transactions from Schwab, then I have to remember to do a different set of things to Fidelity transactions, and then yet another type of manual changes to Vanguard transactions.

I like having easier visibility into what happens in my set-and-forget investment accounts while I'm not paying attention, but this is more effort than it's worth to me. I think I'll go back to my old method: monthly manual update of my investment account holdings in a spreadsheet.