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> “.. from friendly to annoying ..”

My experience as well but I have (so far) avoided “infuriating”. Like other users, I started with Quicken on Windows© XP and was annoyed that it wouldn’t work when migrating to Windows 7, so I purchased Quicken Home & Business 2011 and have been using it since. I also had the same experience (and reaction) as you when contemplating upgrading because I hate the subscription model (Office 365, etc…) and refuse to succumb to it.

So maybe downgrading to a previous version (if you still have the CDs) would work?

I no longer need invoices and such; I used QuickBooks© but that was 20 years ago. Steep learning curve but very powerful.