I currently have a subscription with both Quicken Classic and Simplifi (trying to decide if Simplifi is my future after using the legacy Quicken since 1999 - that's MS-DOS days!) My reluctance to make the switch hinged on the fear of data loss (with all my data on a Quicken server).
Yesterday I contacted Quicken Classic support to help with a "cloud" data issue which accidentally resulted in the deletion of my Simplifi data! In "Classic" Preferences / Quicken ID & Cloud Accounts it shows (2) accounts although clicking on that only the one associated with Classic shows up. THE "GHOST" ACCOUNT IS SIMPLIFI'S which their engineers deleted! Perhaps they don't know about this anomaly? I requested a call back with Simplifi support, and the service rep who called was able to quickly restore all my data (must assume they keep a backup besides the active data file(s).) I only had to log out and then back in to Simplifi in my web browser and my Android app. EVERYTHING was back to the way it was before the accidental account data deletion (my last use of Simplifi). Being a retired IT guy, this tells me that Quicken has the active server's files sufficiently backed up!
I still have until October to use both products (my Classic subscription must be either renewed or terminated then), but at this point Simplifi is in the lead to win! That's saying a lot for an old dog like me to change his ways after using Quicken Deluxe for 26 years!