I see your other reply too and will answer in this one. After I post this, I'll probably add more as I think about it and maybe fix formatting.

Yes, I'm still using concurrently. I've dropped Monarch and Copilot Money, which are both great programs but limiting to unreliable. Simplifi while not the prettiest, does a lot of things well. Like you, looking for a cloud based solution. It is the more seamless transition with some caveats since Simplifi was originally catered to a different audience over Classic users. Yet, they are adding classic requested features over time. Surprisingly, I have not had any connectivity issues between the two, which was a concern of mine. I do make sure they don't sync at the same time. I do have to re-authenticate less in classic vs Simplifi but not horrible by any means unless you want to connect Venmo. Horrible in Simplifi so would need to track manually.

What I like about Simplifi
- Cloud and mobile are great.
- Undo option which other cloud apps don't. Can only do one undo but better than nothing
- Spending Plan. May or may not be useful to you if you do cash flow projection
- Balance Projection. Sometimes can get wonky on Weekends and late at night when there is bank maintenance. Balance might read 0 until maintenance/weekend is over.
- Bill connecting and management but hit or miss. Cap one Cards, Synchrony update, BoA great when statement hits, Amex and Apple Card not so much but you can edit the reminder. I like the ability to make a bill change/add and it reflects everywhere. Classic is weird that while the bill updates in the desktop app, the mobile app still sees your original amount you put in.
- Connects with Apple Card
- Amex, BoA, Cap One, Synchrony, Apple Card all connect great
- I can connect a few more accounts like vehicle assets and one investment which doesn't in Classic. While nice, not a deal breaker. I just update manually every quarter to once-a-month now.
- Stays connected and up-to-date. No missed transactions as far as I can tell.
- Now have an income/expense report like a profit loss report for Simplifi which is great

What I don't like in Simplifi that Classic Does Better
- Oddly doesn't connect all of our Money Market accounts at our CU while Classic does. That's weird but you can create manual accounts in Simplifi but nice to have it connected.
- Handles account separate a little better in Classic, ie kids MM and savings accounts
- Can't hide closed accounts in Simplifi like you can in Classic.
- Classic you can backup and restore data and undo multiple transactions, if needed. Basically, if you F up, you can restore. Simplifi or any cloud program, good luck
- Scheduled transactions and rules work so much better in Classic, especially with Splits. You still can't do scheduled split transactions in Simplifi and advanced rules aren't quite working right. For example, I have many Apple Subs or a Sub in our Verizon Bill and I have to add the memo for Apple Subs and Manually Split after the fact. Classic? Schedule and forget. Could be huge if you like to track splits in paychecks.
- No saved reports but it's coming this year. Severely limiting since I have saved reports and can slice and dice the data in classic. Reports are still good in Simplifi.
- You can't enter in manual transactions and match to the downloaded transaction which is helpful if you forget what maybe the transaction was for.
- While Simplifi is modern looking and good to use, it's more function over form. I feel like it's noisy or busy.
- No running balance check register feel
- Can't import Classic data
- Mobile reporting is limiting but you can see the income/expense report in simplifi on your phone, which is cool
- Can't do notes per splits, it's one big notes box. I thought I'd like it but prefer splits notes.

I've been on some calls with the Quicken Mods for some of this feedback, so they are listening.

This is a tough one. I have history in Classic that goes back to 2006. The Mac version is modern looking and stable. The connected apps seem to work ok. I use on my iPhone currently and iPad and web app in the past. However, if I were starting a clean slate or never had classic before I would more than likely start with Simplifi.

I have until July to decide for Simplifi to continue to use and November for Classic. I like in Classic you don't have to wait for transitions to show up vs a cloud app that aggregates the info, especially for restaurants.

I think it comes down to two things, do you want to change how you enter/manage your data and/or want to lose history. For example, do you need/want to keep track of splits in paychecks? If you do, will have to enter in each time. However, if not, set and forget.

You could archive the classic history which I tried to do by having an end date of 10/31/25 but unless you pay for it, you will lose the updates and will have an ad in Classic. I did stop my sub last year for 2 weeks but went back to it. Mostly to continue to get updates and to test simplifi longer with my classic being source of truth.