Order to upgrades?

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For 300 hp, you can just swap in "059" 305 Vortec heads onto the 305. 3rdgen F body guys do it all the time. If you are keeping the CCC system, a ZZ4 chip and heated O2 sensor are good upgrades. Before any of this, you will want to repair any and all rust damage, poly body bushings, and add on bracing.
 
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IF you're happy with that, and sure you're going to stick with a traditional sbc and not an ls motor, then here's what I'd probably do.

A lot can change in a year or two! Haha maybe I'd push it over 300, but for now I'm not thinking 500+... Regardless, where in your list would you throw suspension?

I do like Streetbu's point about a good looking car making you want to work on it more. Right now, it looks bad... I need to figure out some fender issues and replace or fix the rusted door bottoms before I'd paint it, but I currently hate the color. I do have a set of N95s that I'm planning to powder coat and swap in so I'll have nicer wheels when it looks good enough to do so.
 

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A lot can change in a year or two! Haha maybe I'd push it over 300, but for now I'm not thinking 500+... Regardless, where in your list would you throw suspension?

I do like Streetbu's point about a good looking car making you want to work on it more. Right now, it looks bad... I need to figure out some fender issues and replace or fix the rusted door bottoms before I'd paint it, but I currently hate the color. I do have a set of N95s that I'm planning to powder coat and swap in so I'll have nicer wheels when it looks good enough to do so.
Depends what's broke.

If your sleeves on the tie rods are crusty, or, if they're loose and won't hold adjustment, you need to step up a notch.

Generally, parts are cheap, and I'd do a "rebuild" to stock specs along with the rear end swap.

Add the frame and fender braces off a cutlass and grand prix onto your chassis while you're there.

Also grab 1/2" conduit and sone vice grips, measuring tape, drill, and sheet metal screws. Make two "X" shaped parts by crushing the ends and middle of the conduit. You measure behind your upper rear seat back, what right now is two open squarts with a vertical strip down the middle you're gonna install the x's you made by measuring your openings. Surprisingly helps stop flex and give better traction combined with all the other tidbits

So unless broke. I call it about step 2.5.... really part of 2.

Caveat - if you're lowering the car, I'd wait on the lowering part unless you get some crazy deal until much later in the build.... like the permanent wheel/tire phase
 
I did paint and body first, Serpentine belt swap, 4 speed Muncie, most interior color change and refurbish, ford 9", getting ready to do final dash color change with some air duct work, my buddy has a shop so may side track that to do front end and steering gear work as business is slow. Now I have done a lot of little things to it. Minor detailed stuff that I won't bore you with but makes a ride. Last thing is the engine. Keep it moving and do things that make you happy and proud to be a G-Body owner. I have been driving an El C with a whopping 149 horsepower for 11 years. My motivation was a nice ride and a few more horsepower in the end. I see to many projects that do motor first then fizzle out
 

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