For example, take a simple task: download all your financial data for the last year. Log into your bank's site. There is no button for "last year". You have to laboriously enter 01/01/2015..12/31/2015. Then you're given a choice of formats. Download ALL of them, because sure as shootin', Quicken will only import one of them, and that's one is different for every different account! (Stunningly stoopid.)
Then try to get the statements, just try, my pretty. There is no "get me all the statements from last year." Nope. You download them one at a time, and some of them download to the same file name! So it's clicking around, then rename the file to "January 2015", then repeat for the next one, etc.
Oh, you wanted the tax 1099 forms? That's a whole 'nuther section on the web site.
Buy anything from Paypal? This is the killer. Paypal lists the payee as "Bob". Your credit card statement lists the payee for the same transaction as "Carol". The credit card downloaded data file lists the payee as "Ted". And, Quicken somehow calls it "Alice". Can you believe it in 2016? Naturally, you cannot download the full information about the transaction anyway. Download the CSV file, and Paypal randomly leaves out information you have to manually edit back in, like the item description which appears on the web site but not in the CSV data.
And why does my bank list the payee for a check as "Check 236"? The bank knows who the money got sent too. It's all on a computer.