Hi, Alan.
John Pollard is the expert on linked cash accounts. I've never used Money, so I don't now how it handled such things.
While I've been investing in securities for about 40 years and got into some fairly sophisticated (for the time) investments decades ago, my recent experiences have been quite mundane. My brokers, at least since I started using Quicken in 1990, have all simply kept any cash in the account's cash balance. Well, they have "swept" larger amounts into money market funds - and back - but I've not bothered to track those; to me and to Quicken it was all just "Cash" in the account balance.
Even for Merrill Lynch's Cash Management Account, I recorded all deposits and checks right in the ML investment account, not as a separate linked account. But I never paid expenses with CMA checks and I never deposited income directly into the CMA; I always deposited the checks into my local bank and then transferred the funds to CMA. To pay expenses, I wrote checks on my local banks, then wrote CMA checks for deposit back into the banks. That way, ALL my "external" dealings, both income and expenses, were through my local banks; CMA transactions were only for moving my own money from one pocket to another.
Today, when I sell a stock, the proceeds stay in the broker's cash balance. When I buy a stock, it is paid from that cash balance. When I need cash, or to pay a bill or buy something other than securities, I still transfer funds (by writing myself a CMA check or by calling my non-ML broker and asking him to send me a check from my cash balance) into my local bank and pay the bill (or cash a personal check) from there. Even when moving money from one broker to another, I first deposit the first broker's check in my bank and then write my own check to the second broker. All this makes for a slightly longer paper trail, but the trail is very easy to follow - for me, for Quicken and, if necessary, for the IRS.
RC