Boston isn't great because of building another Kensington. It's great because of its accumulation of history, side-by-side in a vibrant, bustling city. The sign is part of that history. Sure, it's not on the level of brownstones or any of the other spectacular architecture from 100+ years ago, but it's still a fun, quirky piece of history that is unique to our city. (regardless of the corporate mumbo jumbo)
Take it away, replace it with some slap-dick 20 story residential, and we are 1 step closer to another Charlotte, Dallas, Phoenix, etc.
I haven't made it my life's crusade to rid the world of Pokémon even though it's probably the dumbest thing I can possibly think of. I chalk it up to shit I don't understand and move on. (although I do plan to keep it the hell away from my kids) Maybe you young'ins should do the same with the Citgo sign. You don't get it, so leave it alone.