TT certainly has enough idiosyncrasies that I wouldn't change to another program every few years just to save $10 or $20 on the software.
I think that's the case. Sticking with the same program, year in and year out, and you get to learn more about it. At AARP Tax-Aide we use TaxWise which has its own set of issues, but you get used to them. One nice thing is that it is easy to link to the forms. You do not have to go through the prompt mode and you enter the data directly on the forms or the backup forms.
In every case where I was tempted to override, I found the place in the interview interface to enter the right info and numbers to get the number on a form the way I wanted it. That is, I have so far not needed to override any numbers in TT.
That's exactly what I've found. My experience is that I didn't understand the TurboTax question initially and that's why I did not get the result I was seeking.
[Just to clarify, I use TaxWise in my volunteer job, but use TurboTax for my own return.