I last both Quicken Premier 2014 in May 2014 for $45. I think I purchased Quicken 2011 Premier in 2011 for less than that, but I'll use $45 for that as well. so my "yearly" cost has been $15 a year for the last 6 years. In my mind, that is not bad.
I'm looking at more from the perspective of "at what point will a price increase overwhelm the value I have gotten from it?"
I haven't asked any questions to Quicken support, primarily because the few things I ran into someone else had already encountered, and Google helped me find the solution. So for me it is more "how much time do I want to spend tracking my finances?"
I can build spreadsheets. I can write programs to download stock quotes. A lot of financial institutions allow you to download your data in a format that one can easily import into a spreadsheet or manipulate with a program (some provide Application Programming Interfaces - APIs - to access your data, but that comes at a price). The "core" things I use quicken for - tracking transactions and calculating my stocks/bonds/ETFs/funds value - I could do myself, if I wanted to spend the time. And do not rule out the several free Open Source alternatives to Quicken that may be fine for my needs.
So how much am I willing to not have to spend the time to do this? $30 a year? $50? $100? I have to decide. Off the top of my head, less than $50 I could deal with, but that is not with given much thought to it. What is my time worth? And I fine using a free but "community supported" product which might not have regular updates? And if it helps me catch errors equivalent to the yearly amount I pay for it, does that make it worth it?
I'm not saying I like the subscription model... but, I just have to consider the total tradeoff, if I want to stay the course and pay more, go back to "do it myself", or look at cheaper products or free Open Source alternatives.