Stalls in Gear, Automatic- Restarts Good- Can Slam it into Gear! EEEK

The dist should turn along with crank rotation back and forth with only a small dead-band with no motion.
If theres enough slop in the chain, you probably jumped the chain one tooth.
It's now retarded and the engine cannot make enough vacuum to sustain idle at normal speeds. Another clue would be how fast it cranks. If it doesn't sound like the starter is doing the hard work of compression when the engine's hot, but spins the motor fast, that's another reason to suspect the chain jumped and your timing is retarded.
One more question, when you do drive it and let it run up rpm under hard acceleration, did the upper rpm performance seem "improved"?
That also happens if you jump one tooth.
This whole adventure started with a crapy running engine. It missed like a dead cylinder but just couldn't locate the problem. Changed all these components, rebuilt the carb replaced the intake gasket which all contributed in some way to making this thing run quite well in the end even if it meant readjusting the metering rods to increase the idle. The thing is that stumble has not completely gone away and I think you r on to something here. There is play yes in the chain but I can't tell you if that amount is excessive. From my few interactions with internal components such as short block stuff yes the free play doesn't seem right I think. When I move that pulley it's not an immediate transfer to the distributor. This is why I have to now check the timing marks. As for cranking ya I think u r right it always sounded easy to turn over, like this since I first bought it like this. But I also know it's a gear reduction old school starter so that might account for how easily it turns over. As a teen I rebuild dozens of those things as a side note. Up until what I have done it's been difficult to talk about how this performed other than it took long to get to a high enough speed because it would miss so bad it was better to accelerate slowly with the pedal because that made it miss less,if that makes any sense. Had acceleration made it runs horribly. I wonder if I did jump a tooth and possibly a second because I thought I was in the clear on how this thing ran but it's got so bad I can't even take it out of gear as u now know. I don't even think I took it out of the driveway up until this gear stalling business started.