I'm much like Simonmoon in that I can listen in both modes. I'm a modder, so often changing out little things like caps, resistors, etc. After changes I'm initially in analytical mode, if change is positive, I'll segue into music lover mode, this without any conscious effort. I can always tell if a change not good in that I remain in analytical mode. Of course, this sometimes takes time in that both mind and components and/or parts undergo 'burn in'.
Over the years, as my system has improved and matured, I find myself nearly always in music lover mode. As for changes, I've improved my batting average over the years, almost never strike out these days.
I'd agree with another poster who mentioned recordings as a variable for listening mode. There have been times in the past when I doubted my system when listening to previously unheard recordings. If they were of mediocre or worse quality I would go into analytical mode which then led to doubts. As system has matured, thus, subject to much less change, I now doubt my system much less often which lends itself to full time music lover mode, even with those previously unheard recordings. At this point, I have much greater surety regarding recording quality at face value, this lends itself to much more easily entering and remaining in music lover mode with nearly all recordings.