Personally, I would always upgrade financial software, which is going to include new features and bug fixes. At least, Moneydance is a “one-time purchase, including a free upgrade to the next major release. We never ‘sunset’ software, so you can use it for as long as you like without ever needing to pay again.”
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My understanding is that Quicken requires you to sign in when you first launch the program to register it. After that, you can sign out and don’t need to sign in again if you don’t need updates or online features.
Yes, I believe that’s correct. Quicken backs up its files locally. If you want, you can also have them back up to the cloud and share with Quicken on other devices like iPhone. For that you need to be signed in, but you do not have to use that feature.