Just some stuff off the top of my head.
First, if the distributor was in 180 degrees out, it wouldn't start. You'd have backfires thru the carb and the exhaust. This is a good way to get a new exhuast system. I know, I need one now.

I'm very good at installing distributors exactly 180 out. 9 times out of 10.
Second, about timing advance. First of all, do you have a vacuum advance can? If so, you should be able to see the arm from it moving as you blip the throttle. It should advance the timing at part-throttle. Then there's the centrifugal advance. Are the weights rusted so that they don't move? This would prevent advance from coming in as the engine speed increases. You can check them by removing the distributor plate...they're underneath it.
You mentioned an electronic ignition. Is it an HEI with the coil in the cap like this one:
292 with HEI ? Or is it a Pertonix conversion like this one?
Pertronix If it's an HEI setup (like what I'm running on my 292) it's a [censored] to get enough room to turn the bulky old thing to get sufficient timing advance. I've had to rearrange the fuel line so that I could turn the distributor a little more and get it set where I like it (timed it by ear.)
Btw, I had the distributor clamp bolt loosen up on me and it allowed the distributor to rearrange itself. When it did, it retarded the hell out of itself. That led to really poor performance. It would start, but have trouble idling. And it was virtually powerless as I engaged the clutch....until it got wound up a little bit and the centrifugal advance kicked in. Once I saw what had happened and twisted the distributor back where it was sposeta be, it ran fine again. So fine, as a matter of fact that I decided to put a 4-barrel carb, split headers and Purple Horny mufflers (I've got a pair just sittin around) on the thing...especially since I need to replace the exhuast anyway.
One final thing to check. Is the vacuum hose to the vacuum cannister connected and in good shape? Any possibility of a vacuum leak? This could cause problems of the sort that you're describing.
Good luck with it.