Just read today’s email about Quicken. I was an MS Money user until MS pulled the plug on it. The only choice for a non-web based tool was Quicken. I hate that, in a money grab, they went subscription. Quicken is an inferior product to MS Money but the other products are even more inferior. I’ve yet to find one that is as simple to use for compiling spending reports and tax data. It is far from perfect, however. It routinely guesses wrong, way wrong, on interpreting downloaded transactions. I frequently have to go online to my banking web sites to track down what a given transaction is for. I wish MS Money was still viable but Quicken is really the closest thing to it out there.
When my Quicken version went out of support about 20 years ago, I switched everything to Excel. I run multiple real estate corporations using just transaction ledgers and pivot tables. I also wrote some custom macros so that for common ledger entries it pre-populates all of the income statement and balance sheet reference attributes. All it took really was investing the time to understand the Form 1065 and Form 1120 and how they report information.
My first Quicken copy came from my bank on a 3.5-inch floppy. Yes, I’m old!! I still use Quicken today, and I love it. Sornord is correct; it often guesses incorrectly in regard to transfers, but that is minor compared to all the good it will do you. When it comes to tracking income, payments, loans, assets, and almost everything else, it is almost foolproof.
Investments, I don’t think it is very good at that. Especially when it comes to investment reports. I built my own Excel sheets and download the data from Etrade. I ran an LLC on Quicken for ten years and had zero issues.
I highly recommend it.
I’m still using Quicken 2002 from a DVD. It has worked up to Win10. I am on extended support so I will have to upgrade to Win11 in October. We will see if it still works. I only use it for personal finance and I can still import my CC statements. I just have to import them as CSV into Excel then use a little Excel plugin to convert to QIF which the old Quicken imported.
Using Quicken many years.
I have over 8,000 scanned receipts. 
Have you tried KMyMoney?
I have been using Quicken since the 1990’s and I am still very happy with it. It downloads transactions from 40 or more institutions every morning except Sunday and Monday since the markets are closed on the weekends. They answer the phone now since you’re paying every year.
I have used MS Money in the past and although Quicken does have some imperfections (and I hate the subscription model), it is definitely the best alternative to a non-web-based product out there today. It may also misreport downloaded transactions occasionally, so be sure to verify receipts against your bank statements; however for generating reports on how much you have spent and all necessary information for filing taxes, Quicken is the best option available.
The reports it can generate are the only reason I still use Quicken.
My ex just got it for her Mac. That was one the first things she noticed about it…and loves it. She had it on a PC that her assistant used for her business (realtor). She wasn’t aware of that feature. Now that she has it on her own…she may catch you by the end of the year!