FWIW, what I do:
I'm still a Luddite who has no downloaded transaction data in Money. About 100k transactions later (depending on how you count), mine are all still by hand. For Investment Accounts, I take one or two steps to assure I reconcile with the downloaded .PDF statements from Fidelity and Vanguard. (It's complicated why I have both of them. I used to have more FIs when we had 401(k)s and 401(k) SMAs. It's still two brokerage accounts with Investment Account associated Cash ("InvCash") accounts, two IRAs with InvCash accounts, and two Roth IRAs without InvCash accounts.) If I see a transaction online, I generally "C" mark it in Money. If I enter a transaction in Money because I saw it online, I try to be more conscientious about "C" marking it.
I balance the non-retirement InvCash accounts monthly using the Money InvCash More cash tasks...Balance an account native tool and the downloaded statement .PDF. This is no different than balancing any other Money cash-type account. Since one of the affected accounts is used as our checking account and the other is all but dormant most months, this goes quickly. For the two InvCash accounts associated with the IRAs, the "Balance an account..." choice brings up the dreaded "Update retirement account" "Wizard". It's terrible because it has bad side effects. I can't remember details--there may be a FAQ Q&A--because it's been quite literally decades since I tried it. I balance the retirement InvCash accounts by hand. The number of transactions here is minimal.
I balance share quantities in the Investment Accounts vs. share balances shown on the statement .PDFs quarterly. (Money doesn't provide a tool to do this for non-retirement accounts and the tool they provide for retirement accounts is, as noted, garbage.) I use either the Investment Account Summary view or Portfolio Manager Standard view, with an appropriate As Of date, to see the Money # shares balance and match that against statements. Those that don't match get further investigation. Once they match, I "R" mark all the Investment Transactions that are included in that balance. The only headache is that we have some positions that Fidelity only reports after the fact with backdated as-of dates. (I.e., the transactions aren't on this month's statements, but are in next month's statement share balance and are transacted at the as-of-date price.) These only cause a problem if I record Investment transactions, typically a Reinvest * transaction with a share qty, in Money, at the as-of date, before I balance to the statement ending that same as-of. In those cases, I typically either use the Portfolio Manager As-Of one day earlier share balance or, if other transactions with share qty impact on the as-of date are on the statement, I temporarily Void the "post-statement" transaction, balance shares, then un-void the problem transaction. Cases with share #s out of balance are, in descending order of likelihood, because a) I fat-fingered a share qty when entering a transaction, b) I missed entering a transaction, or c) I entered a transaction order at a guess price and never updated it when I got a confirm/online visibility to how it executed.
To keep investment position values "balanced", I update share prices manually for positions I hold. I do this as often as I see fit/have a need in for a precise account value Money, but typically only for the last market day of every quarter. Night before last, that was 15 quotes read from a browser window and typed into Money Update prices manually.
Your mix of accounts, transactions, investment types, and your trading practices all affect the choices that will work well for you in how you capture transaction information and make sure it stays consistent with the reality at the FIs. What I describe works well for me. Maybe just because I'm used to it.
On Sunday, January 2, 2022 at 5:35:31 AM UTC-10 Cal Learner wrote:
A few times a year I balance my investment accounts by balancing the cash. ...