I think for frequent visitors like yourself, planning based on ADRs (if you choose to do them) is less of an issue. For the "once in a lifetime" or very infrequent visitor, it's much more important to get those "big" ADRs in there. Our last trip was "once in a lifetime" or so we thought.

so we "had to" do CRT and Chef Mickey with our DD5. If you go two or three times a year, there are more opportunities to do those ADRs that are a big deal, or really special.
Our last trip was booked at less than 180 days out, so I had to really simultaneously decide which parks for which days, and which ADRs we would do - no more than one TS per day. We got every single ADR we wanted, all at times we wanted: PPO CRT, a Chef Mickey breakfast, PPO BOG, and a few others that aren't as hard to get. Some of them I had to keep searching for, some of them I got on my first attempt, and my TA snagged the BOG in the middle of the night.
Our next trip is 10 months away. We need to plan around which night we will go to
MNSSHP, and not going to Epcot on Friday, Saturday, or Sunday because I want to avoid the F&W crowd. The only hard to get ADR we really want is PPO BOG, and we want it because we really liked the food, not to get a jump start on anything. There's nothing else on our "must-eat at" list this time, so we're a bit more flexible. We're also on a much shorter trip this time, so we can't afford to be as stubborn about where we want to eat.
While our last trip was "we're never coming back again" before we got there, this time we know we'll be back again someday, but it won't be for a while because we have too much going on, and too many other places to travel that we're already planning for.