Suggestions/help for my 440 build/swap

Yes its pretty tight with a RB in an A body. First time I did it I said I would never do it again... then I did it again. Everything is harder, but nothing is really impossible with a little creative thinking or a friend/child with really small hands! This time I went low-deck, which made it a little easier. I see you already have the 440 so go with it!

My only advice based on what you said would be Schumacher headers over the TTis (I've ran both and life is just easier with Schumacher, since you said mostly street) and whatever cam you are thinking you need for that lope, go down a size or two. It wont take much cam for a fun RB a-body, but over-camming is really easy to do (been there, done that), plus needing a looser converter, steeper gear, and more initial timing.

For cooling, i struggled for a year experimenting. Then I did a dual row with 1" tubes from ECP and the Ford Contour electric fans (trimmed to clear the water pump pulley) and never had an issue again.