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All else being equal, what power gains could be expected from Trick Flow 240s over Edelbrock heads on a 500 cube mill ?

Leaning over the fenders is a pita. Pull the engine and do it on a stand. Heads off, new gaskets, etc.
 
This whole idea was characteristic of my over-active imagination. I often like to let my mind wander and think of a variety of what if I did this scenarios.
Most of the time I don't follow through. Sometimes I do though.
I thought for years about a roller cam swap and I finally bought the stuff to do it. The same applies to the 5 speed conversion.
There are points that can be made in a Pro/Con list.
The biggest Con is the cost for the increase in power. $3000 for about 30 HP is hard to swallow.
One thing that got me considering this change is that to make the switch to the roller camshaft, I need to change the springs and seals on all the valves. I'm faced with doing this with the heads still in place so I'll have to pressurize each cylinder, crank down my hand operated valve spring compressor, change the valve stem seals and springs while testing each one for height using a box of shims and I'm not looking forward to that. It seemed like just changing the heads would be easier, though expensive. I considered the fact that I could just pull the Edelbrocks off and do the work on a table.
My better sense tells me to just "man up" and do the work on these heads because the cost of the Trick Flows is so high versus the gains I'd see.
I like keeping everything under the stock hood so that means no TF 270s and the matching single plane high rise intake. Given that, the TF 240s with my Performer RPM intake limits what gains I could have. I'm already close to the hood now.

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Nice paint!
Back in the early 1990's I ran into thoughts like this.
I had over-reved the original 383 in the Charger and bent a few valves.
At the time, Koffels had recently introduced the B1-B/S heads, and thinking the small 65cc chambers would give the 383 a compression boost.
Then started looking that to take advantage of the extra flow of the heads, I would need a bigger cam, and the 383 only had flat tops with no valve reliefs.
So the 451" stroked 400 was popular then using a machined 440 crank and rods, and ROSS was making pistons for the combination.
Anyhow ended up building a complete different engine just for the cylinder heads.
Things were a bit different back then. No internet, had to request parts catalogs through snail mail, or by going to car shows where the vendors would give (or sell) parts catalogs.
There were no inexpensive new stroker cranks, and no "kits" that I knew of. Chrysler Power magazine had done a few 451" stroker articles using the 400 cast pistons, and ROSS was just starting to make forged pistons for the combination. Head choices were pretty limited to factory Iron Production, The Original Indy cast iron 440-1, Mopar Stage VI, the B1-B/S, Stage V Hemi conversion, and I think the Bulldog head? It would be around 10 more years around 2002? that Edelbrock would have the Performer RPM heads, and maybe longer before KB/ICON would start making stroker pistons.
 
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