>>120855930You'll pick up on recurring themes and gags as you go. Some stay throughout basically the whole strip (the football gag, Beethoven's Birthday, Charlie Brown's baseball team, Snoopy's excitement for suppertime), some only stick around for a few years (Linus trying to remember his lines for the Christmas pageant, Poor Sweet Baby, the 6 Bunny-Wunnies, Violet's mud pies), and some disappear and reappear with giant gaps (the World War I Flying Ace, the vulture, the Little Red-Haired Girl, Pig-Pen in general).
You'll never really meet all of the main cast. There are characters introduced in the 90's who make regular appearances until the end.
As for your peak canon/timelessness question, I'd say it doesn't exist. People often say mid-late 60's since that's when A Charlie Brown Christmas, The Great Pumpkin, and A Boy Named Charlie Brown came out. This was the peak of the series' popularity. However, there are a lot of iconic elements that wouldn't be introduced until after that (Woodstock's name, Joe Cool, the Easter Beagle, Peppermint Patty and Marcie's love triangle with Charlie Brown, Sally calling Linus "Sweet Baboo", Snoopy reconnecting with his siblings).
One more thing, this just may be personal preference, but I think 2 years a day is digesting it too fast. Remember, the strip was designed to be read one a day. Back when I read through the whole thing, I did two months a day, but on some days I'd watch one of the animations instead or fill it with some other supplementary material. This took me around one year to finish, and it was a decent pace. If you just want to read through it as quick as possible, then I'd do 6 months a day at most. Too much changes in 2 years to fully process it in a single chunk.