I didn't want to hijack the thread "What does Quicken mean to you?", but this a side question I think about when I think of that question.
My answer is I wouldn't recommend Quicken to a new user until their finances get pretty complicated. The learning curve is very steep in Quicken and there are many new features that will attract a new user's attention that will be their doom because they expect it to work without problems and without limitation that are there and not apparent.
When you look at the people on here that report the least amount of problems it becomes very obvious it tends to be more about the features they don't use than almost anything else. The second part is understanding things like the fact the tax predictions based on a paycheck reminder are going to be wrong if your paycheck is going to change during the year for things like maxing out the social security tax, or 401K contribution, or maybe you are a contractor or a teacher. And knowing that features like the Lifetime Planner or the Capital Gains Calculator haven't been maintained, … And understanding that given the lack of standardization in the financial institutions, billers, and such means they will never be reliable for a large population of customers. One tends to forget that 99.99% reliable means that one in ten thousand will have a problem and when you have hundreds of thousands or even millions of customers that isn't a small amount of people.
I would be much more inclined to recommend something like Simplifi.
To me this question has changed over time. Back when I first started using Quicken what the financial institutions provided was pretty weak, but it has got a lot better. So, in fact, I would have been more willing to recommend it. Not only is it because the lack of tools back then, but also because Quicken had less features that might trip up the users.