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Is this the same car that had extra gaskets in place? If so, you may well have false air screwing things up. Make that stuff correct if it isn't already.
Have you cranked the engine over with the valve cover removed to confirm that the valves are actually opening and closing? If not, do. Maybe your engine has one of those crappy soft cams that hit the market several years ago and lost its lobes. Look to see that the rockers are all doing about the same thing. Don't worry about precision - if you've got a flat lobe (or two or more) you'll see it.
Battery's hooked up the right way, right?
Okay:
If it's puffing smoke out through the carbs, then the plugs are firing while the intake valves are still open. Which means the ignition timing is way off. Either the method of static timing you're using isn't working, or something about the execution isn't quite right.
Simpler timing method: have an assistant crank the engine over while you set the timing using a timing light. It probably won't be exactly perfect, but it'll be really really close. Plenty close enough to start the engine. And you can move the distributor while the engine is cranking, which is a lot easier than moving the distributor a little bit, then trying to start the engine, then moving the dizzy a little more, then trying again, etc.
Put the timing light on the coil wire instead of the wire leading to cyl 1. Then you can also check to see if you have a regular - or erratic - misfire.
Given the amount of cranking the engine's had, take the plugs out and squirt some oil into the cylinders. Enough that it'll soak the rings all the way around the pistons. There's a good chance that fuel has rinsed the rings and you're now facing a lack of compression. Yeah, sounds like a long shot. But I've seen it many times before.
If there's any chance at all that the ignition switch (or connections to and from it, or the wires connected to it) is/are at fault, bypass it completely: run a wire from the positive terminal on the battery directly to the coil. At this point, the ignition switch will only be used to engage the starter. Note: if the engine starts, you'll need to pull this "hot" wire to shut it off.
If you have a Smiths tach, remove it from the ignition circuit completely until the engine is running well enough to merit the use of a tach.
So: 1: oil the cylinders.
2: install brand new NGK plugs gapped at .025 - .027". It's true that you can run a bigger gap, especially when using breakerless ignition, but all you're really doing is making it harder for the spark to jump from point A to B. If anyone reads this, they'll likely disagree with me. Trust me. When we dynoed Phil's MPPE, we picked up several RWHP at high rpms by decreasing the plug gap in his engine to .025". Don't use fancy platinum or other whatever BS sales pitch plugs they're trying to sell you: the electrodes are small and prone to fouling. NGK BP6HS.
3: Do what you can to static time the engine.
4: Pour a little gas into the carb throats.
5: Have your assistant crank the engine over while you use the timing light to get the ignition timing close to ideal. Shoot for something around 15 degrees to start with.
If the engine starts, celebrate. If it doesn't, leave the timing at its indicated 15ish degrees and have the assistant crank the engine some more while you spray starting fluid into the carbs.
Now it should start.
[Tangent: Tricky thing about the Crane is getting it "phased." You can get the engine to TDC and have the rotor right exactly where you want it and have zero luck starting the engine if the Crane isn't "phased." Pain in the ass, but necessary.]
Good luck!
Cameron
Rose City
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