I've done a bunch of searching/reading, so I think I might have found an answer, but would like to confirm before I go spending more money.
First off, I'm working with a 1949 216 that I believe is 100% stock, and has a Carter W-1 carb. I've been struggling with a bunch of starting/rough-running issues over the past year and I don't think I've found/fixed the root issue yet. Last year I replaced the coil, which didn't seen to help. Then I did a complete tune up, replacing the plugs, wires, points, cap/rotor and installed one of Jon's new design condensers. I had the truck running great after that, so I thought I had it fixed, even though I never knew what fixed it. Then one day not much later I had the truck out idling for a bit on it's own and it stopped running. It would not restart. I've been trying ever since to get it running again. I suspected my ignition switch might have gone bad, but I've bypassed it for the time being with a wire directly from the starter terminal to the coil and a light switch

It definitely seemed like a spark issue, so I've never touched the carb.
Today I noticed the points were not closing evenly and were only making contact on the outer edge. I installed a new set of "Blue Streak" points and in the process noticed that the electrical connector on the condenser may have been touching the distributor base, or potentially close enough to arc. I'm guessing these two issues were resulting in a weak spark. I finally got the engine running, but the idle is bouncing around and when I try to increase the idle it runs very rough. The timing and dwell are both erratic. The dwell looks like it might be set to about 38, but it bounces around and drops down to as low as 25-ish.
In searching on erratic dwell, it seems a bad distributor could be the issue. My distributor does have a bit of side-to-side movement. I'm not sure what amount is allowable, if any? The uncertainty I'm having is that I had the truck running pretty good, with a steady dwell just a few months ago. It doesn't make sense that somehow now the distributor is the problem. Is there anything else that could be causing erratic dwell, erratic timing, and a bouncing idle?