One day it sorta layed itself out before me:

Heavy as a Really Heavy Thing was a simple "what am I capable of" test. City was a total freakout and Ocean Machine was the reflecting "let's calm" attempt, pushed beyond limits with Infinity. Physicist then was to resolve Infinity issues but failed miserably. Terria was the aftermath. On SYL Dev didn't touch that issue, also Accelerated Evolution was a direct attempt at denial and only with Alien Devin managed to come clean with himself. Synchestra was then the calm closure. The New Black is just having fun with looking back at it all.

I could make this a two page essay, but that would be just adding useless poetry. Comments?

Physicist then was to resolve Infinity issues but failed miserably.

Comments?

I disagree. Physicist was an album Devin made in the grey haze that he was left in after crashing down from making Infinity. I don't think that it was meant to resolve anything, and it DEFINITELY didn't fail miserably as an album.

And Terria is clearly a work unto itself, not the aftermath of anything. I don't see Terria having anything to do with the Infinity era at all. I don't see why you think that everything after Infinity was just an attempt to resolve some issues. I think that by the time he did Terria, the mess that he might have been during Infinity was a thing of the past...

i think its overnalyzing it

From what I've read, your theories are quite possible.