[Edit - QPW beat me to many of the comments below]That is an interesting idea, but may be difficult to implement, because in my experience each brokerage has a different way of grouping the securities, and sometimes even variations on the name for the same security - is it Home Depot or The Home Depot Inc.? Also some include tickers in statements and some do not.If you are downloading from the brokerage, you can go to Edit > Preferences > Downloaded transactions an next to Compare Account Portfolio after Download, click on Edit Settings and select the accounts you want to compare. With this setting, Quicken will compare its holdings to your online portfolio every time you download and identify any discrepancies. Rather than letting Quicken create any Placeholders, I resolve the discrepancies (usually due to a round-off error) before proceeding. This will keep Quicken's data in agreement with the FI as you go, rather than waiting till there is a statement.Also at any time you can click the gear at the top right of the transaction list (register) and select Reconcile Shares. and it will compare Quicken's holdings to the downloaded numbers.If you want to compare to a paper statement, you can make sure your downloads are up to date then click on Holdings and set the As of date the to the statement date. For me the account value usually agrees with the statement to the penny so there is nothing further to reconcile. If there is a discrepancy, then you do have to compare the share counts for each security, which can be tedious. For me it is usually easiest to print out both lists and check them off as I go. One trick that sometimes works if you are looking at the account online is to sort the holdings in value order from largest to smallest and put the list in Quicken in the same order. That reduces the amount of jumping around in the lists.If the share counts agree and there is still a small discrepancy in the balance, I don't generally bother tracking down small price differences. If you want to do this, you can still take advantage of the ordered list as mentioned above.
I believe that there are only two important # for each security, basis and # of shares. Trying to compare a security at Market Value (Q vs brokerage) requires that both sources of information have the exact same quotes, do you really care about that? It just makes the process harder.As QPW stated, Quicken does the # of shares compare at each download. For the basis you have to make sure that you enter the correct total cost when the security is purchased.
there are only two important # for each security, basis and # of shares
There should not be any rounding errors if you enter the distribution reinvestments with the correct share amounts.