QUOTE(bearbear @ Sep 4 2016, 12:50 AM)
Yes you get extra 500XP (x2 with lucky egg) if you evolve something you never caught
but your candy cost will be more than double to evolve pidgeot. (50 vs 12) You can effectively upgrade 4 pidgets (48 candies required) vs 1 Pidgeotto (50 candies required)
so my advise is still spam evolve pidget, as your aim is to get more XP and lvl up.
Once your level is higher you are bound to find these pokemon in the wild somewhere, or you can just evolve one for collection.
QUOTE(Quantum_thinking @ Sep 4 2016, 01:23 PM)
The goal of mass evolving is to get the necessary experience. Hence, i always evolve the pidgey, caterpie and weedle as it is the "cheapest" to evolve.
However, i tend to look out before i trade off my Raticate as some of them may have a very high damage attack for their Hyper Beam. For the Pidgeottos, i just trade them all.

it may come as a surprise but I don't see a lot of caterpie and weedle. Pidgey is more but still not that many.
I got most Drowzee candies (310), Ratata (258) and then Pidgey (244).
currently I can do 47 evolution. I'm waiting until 60 then I'll use lucky egg.