I've been a user of Quicken for decades. I'm a fan of the overall approach, and have (currently) no difficulty with how it models my financial data or the interface FUNCTIONALLLY.
The problem is performance. I have done all the hacks. Try to archive accounts, validating, super-validating, blah blah blah. Quicken is fine with small quicken files. But when the files get large, with hundreds of accounts and tens of thousands of transactions (especially investment transactions) it just chokes.
It is annoying that quicken keeps adding feature updates but seems (so far) unwilling to undertake the work to overhaul the un-sexy tech debt problems underpinning painfully poor performance.
As a software engineer myself, and one who often has to deal with tech debt, I can see that there are two major tech debt problems. One is the interface with the Windows OS and in particular the mechanisms for repainting on the graphics driver. The screen flashes on and off, windows and parts of windows are unnecessarily repainted multiple times, and the graphics rendering itself is inefficient and low-fidelity. I'm on a machine that can flawlessly play video games in real time, but Quicken flickers and halts and chokes, even when it is the ONLY interactive process running. The other big tech debt problem clearly is the efficiency of dealing with its own data model and database. It is clear from looking at the metrics that Quicken doesn't scale well with its own data implemented in its own files. Access is slow and cumbersome, and if you look at the disk reads and writes, there is WAY too much going on. My hypothesis (which of course I cannot prove) is that Quicken is using its own database technology for file access written years ago, and not up to current technology standards and not employing efficient data design and data normalization.
I realize that fixing this kind of tech debt is expensive and time consuming, and difficult for QA, and many customers won't notice that the upgrade adds a feature or fixes a bug. In fact in the short term, it is likely to add some regressions. But it is really time for Quicken to get a major infrastructural overhaul to deal with the incredibly inefficient and poorly performant issues. We are paying subscriptions now for this software. Please divert some resources into that.