80s and 90s til death for me.
Subaru sucks now, they are just toyotas with flat engines now in my humble opinion.
I have owned a 99 outback, they are solid cars but not my cup of tea. They are fantastic grocery getters but too big and underpowered for crazy off roading.
To answer your questions, i feel that the last year of the pretty Subarus was 94, the first gen legacy and impreza. It's funny that Subaru was always on the opposite side of using alphanumerics. The only body styles i would consider buying are those, from the 80s when they were actually unique. GL, DL, XT BRAT etc...
I do love the early ej engines. I have a 95 ej22 in my 86 GL and i love that combo. +1 on the dual range transmission, i was buried up to the pumpkin in snow and a little digging and she beasted out of snow so deep the door wouldn't open. She's pretty sleeper now, actually faster than my 77 camaro in a drag race.
If money were no object, i would sti swap my 85 xt, but it is and i think i would LS swap something first.
Oh and three pedals only except for a th350 in my old rv. :-)