340 or 408?

True if those things matter to the OP or not, if streetability and rpm ain't a huge deal to you then the advantages of cid might not be a huge selling point, depends what the OP wants. But yes seem most generally would prefer the advantages of cid.

They should/could be putting similar torque to the ground.

The OP should have no shortage with torque even with 340 and 4.56.

say at 1.25 lbs-ft per cid

363 x 1.25 x 4.56 = 2069 lbs-ft
454 x 1.25 x 3.55 = 2015 lbs-ft
Okay. Now do the 454 with 3.91s. (I'm putting 4.10s and a spool behind my 540)