440 swap in 66 cuda

Necessary? Maybe not... but you WILL want them.
If you are serious about this swap, start shopping for fenderwell headers now. I would also look at the Schumacher tri-y's, they just might work, and would be better than any manifolds that could be made to fit
And if it was my project?..... Andy F's elephant ear motor plate would be my first purchase. I can be rubber mounted if necessary. I wouldn't bother. That just might give you enough room for under chassis headers or tri-y's.
totally agree. at this stage of the game, if i was messing around with something like that i'd just straight to a motor plate/elephant ears.

if i was throwing stealth to the wind and didn't care about it coming off the least bit stock, i'd 100% bite the bullet and go with a hemi denny front set up, or at least t-bar delete and motor plate it. then there'd be all kinds of room for activities. that would allow for some reinterpretation of the fenderwells at least, and open up a few choices for headers.

like any big bock swap, after getting by making everything fit the biggest issue (and cost) is exhaust.