If I decide to put a 455 in A 1987 442 how many headaches will I have? And are headers available for that match up? If a street strip 2004R trans wont hold up what headaches are involved in installing a turbo 400.

 

Guess 'the kid' wants to go ***** out, huh?
Headers might be a small problem, compared to twisting the frame, cracking/breaking the rear of the frame, as it goes up for the rear wheels, etc.
I can only compare this combination with the BB powered late [78-82] malibu's, and what I've heard about their problems.
Don't know if you've checked out the complete frame, but being a Wisc. car, I'd be doing exactly that, first!
It's easier to reinforce something straight, before it's broke and/or twisted by torque.
Being a T-Top car, you're already loosing some strength, and a 'twist' could make the t-tops inoperable, doors out of whack, etc.
If it was me, I'd be building a 350 - and keeping the 307 all in one piece, for resale sake, down the road.
Now, if it was just a run-of-the-mill Cutlass, that'd be a different story!
A T-400 might need a little 'massaging' with a BFH on the floor, but can be installed with a shortened driveshaft and different yoke, but where do you stop?
Now the weak link will be the 8 1/2" rear, if you use sticky tires, it won't last.

Might be better to restore this one as stock, sell it and have much more to play with on another.

 

Kid does dad does not. Cost of headers alone is crazy and still a pain to install. And all what you said is just what I told him. Had the same problems with the 77 I did that with, trans problems, drive shaft problems, rear end problems, etc. I stopped driving it when I twisted the bell housing into pieces one day, then it was parked. Dad still thinks putting a 350 in is the way to go. (less headaches) And I did plan on keeping the 307 in case we decide to sell later, But I doubt that will happen. I am just looking at all the options before I start in one direction or the other. I kind of like the one guys idea of painting a 350 black and claiming its a 307. LOL

 

Hope he's not reading this - -
Build him a 350, maybe 350-375 hp and let him get his feet wet, and see what it takes just to handle that kind of power!
That's enough to keep him ahead of 95% of what's out there, except Motorola!
Don't forget, as of 3/1, Illinois makes it a felony if over 30 over - car gets impounded!!
If he still has a license, hasn't had an accident, and still unsatisfied, there's always nitrous!

 

That was my idea with the 350 painted flat black.

I like the 78-85 Delta 88's and 78-90 CC's which are not known to be performance cars. With an engine painted factory color, I'll have a sleeper and something that I can show at a classic car show as an all stock car.

Yes my car will have exhaust done to it, but EVERYBODY has aftermarket exhaust today