Quicken Basic for the first 5-10 years, then Quicken Deluxe. I run manual reports out of quicken as a cross check to do taxes. My taxes are all done in my own personal excel file that I've developed over the years - initially as a calculator and then I've been adding on to "automate" it. I've spent more time "programming" my tax form, using excels built-in formulas only, than maintaining Quicken.

For Quicken, I've probably spent 8 hours per year just on setup and then managing accounts. At this point, a majority of my accounts automatically update.(~25), a few require me to update by downloading transactions via web interface (4), and a few require me to manually enter:
Synchrony Financial Savings Accoutn
HSA account (none of these have ever loaded automatically or semi-automatically) - since non-tax bearing,that has been fine
Pension fund (not much to track, I just update one/year manually in 10 minutes to include as Net Worth)
Virginia 529 Vest Account (manual update, not too many transactions - I just checked to make sure that hasn't changed and it's still manual)

I'm pretty well vested (or invested) in Quicken and will continue to use. There have been times when I've been frustrated with glitches, but I've learned how to get by them. The biggest trick is to fix an automatically downloaded account, you need to turn off automatic download, delete the financial institution name, your account information (user and PW), and then exit quicken. If you don't exit quicken, it does not reconcile that change and future efforts to re-automate and account will most likely fail. Why do they fail to begin with? I think mostly it is due to financial institution software and security changes that require a reset of the account login process.

I do not use the online version and as far as I know, I've checked off any online data storage. I did look at mint a few years back before renewing Quicken. It is free and web based, but I decided I was happy enough with Quicken to continue.

I attached a screenshot of my Quicken Deluxe purchases for cost reference. I would watch for discounts so add $10 to those numbers get a rough cost (if you don't wait and look for sales). The licenses used to be for 3 years, but now it's annual renewal and the price has increased a bit. Feel free to ask any questions. I can post more report info (minus personal information) if there's something you are particularly looking to see. Not that two years of purchases are not reported (2014 and 2017) as they were done via amazon.

[Post edited by Hokie Hokie at 01/09/2021 09:28AM]