I started using Quicken last week, one of the brokerages I use doesn't support any of the online connection methods and I can't seem to figure out how I should categorize the transactions on the online side and offline side to make everything resolve properly.
Issue # 1:
Monthly investment from checking → investment account. The checking account is online and pulls transactions. I tried marking it as a Transfer→Investment account. This ends up showing up as a Payment/Deposit transaction in the investment account and adds to the cash holding in the investment account (even though in reality it goes straight to shares). So I go in to manually enter a Buy transaction in the investment account to move the funds from cash to the security. If I put in the total, but leave the #shares blank, expecting it to auto-calculate based on the daily price (mutual fund), it leaves it as 0 shares. If I look up the full transaction details I can make it reconcile, but its feeling like I'm making extra work for myself, but this might be the correct workflow.
Issue #2:
When I setup the offline brokerage account, its listed as a live opening balance that should auto-correct for pre-dated transactions, but since they are also transfers(Payment/Deposit), the predated transactions just blows up the cash balance and messes up the actual opening balance.
Thanks in advance for any tips y'all have.