When a company is told they need to switch to a different architecture and five years later they still have not, I do not have a good feeling about them. It's not like TurboTax (and other Intuit stuff, H&R Block, etc.) came from a guy living in his mom's basement then got a job at Taco Bell, so now he doesn't have time.
I also don't want to hear "It's a huge undertaking and we need a ton of resources to get this done." I have been involved with software development in some shape or form for quite a bit of my life, and in my experience, it seems much of the expense is not in the actual coding; rather, it's in the dreadful meetings deciding exactly how it will do things, what it will look like, those kinds of things. That stuff is done.
Finally, I have to wonder if they -- Intel, H&R, etc. -- executed buzzwords like "agile" and "sprint" to mean "Bang out some code and get it out as quick as possible and don't bother to comment/document or think about the future." This ends up with a phrase many developers are all too familiar with: spaghetti code.
