Distributor won't drop in fully...

If cleaning it up doesn't do the trick take a flat file and pass it through the female slot of the distributor shaft making it a touch wider. It's okay to have a little "slop" at the union.
You might have to resort to using some emery cloth around the end of the shaft to reduce the diameter a touch but that would be unusual for that to be necessary.
 
If cleaning it up doesn't do the trick take a flat file and pass it through the female slot of the distributor shaft making it a touch wider. It's okay to have a little "slop" at the union.
You might have to resort to using some emery cloth around the end of the shaft to reduce the diameter a touch but that would be unusual for that to be necessary.
I’ve had a couple of replacement lower shafts that had this problem, in my case it was at the collar at the bottom of the distributor, not at the oil pump gear. I removed the collar and found that the width of the slot was good but the offsets didn’t line up so they wouldn’t mate. I ended up chucking the shafts into a lathe and taking a couple thou off the diameter until they fit in the collar properly. Whatever tools you have access to.
 
Speaking of removing the Distributor, if I take out the locking nut, is anything going to fall down into the engine, I need to remove it to install the Pop-Out ignition switch.
 
Speaking of removing the Distributor, if I take out the locking nut, is anything going to fall down into the engine, I need to remove it to install the Pop-Out ignition switch.

No, the purpose of that nut is to keep the distributor from coming up out of the head due to vibration. Just do your best, when you remove the distributor, to keep the shaft in the same position the whole time. That'll speed up the process of reinstalling it.
 
Thank you everyone for your help, and retrospectively it turned out to be the problem with the collar on the oil pump drive gear assembly. I say retrospectively, because I now have another, seemingly worse problem. The stainless-steel distributor shaft is now firmly jammed into the top of the pump drive gear.

I cleaned around the collar and inserted the shaft, not noticing that it was positioned 180° from where it should be (at this point I wasn't thinking straight). When I tried lifting the shaft out to rotate it into the proper position, it wouldn't budge. No matter how hard I pull on it (using a double-X extended reach needle nose pliers), I cannot get it to come loose. Now my question is this... If I remove the valve cover (this is a "B" block engine), will I be able to access the collar from underneath and pry the distributor shaft and drive gear assembly apart? I don't care if I damage the drive gear or shaft in the process because I plan to replace them both anyway. What I'm trying to avoid is getting under the car to remove the oil pan and slide the whole pump out. I have physical limitations preventing me from getting under the car. Thanks in advance for your help.
 
The short answer is probably not as it's hard to get to the lower shaft because of the spring that hold the oil pump drive gear in place. I had one that was really stuck and I had to make a collet puller to get it out.
 

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The short answer is probably not as it's hard to get to the lower shaft because of the spring that hold the oil pump drive gear in place. I had one that was really stuck and I had to make a collet puller to get it out.

That's a great idea, but where would I get something like this?
 
The short answer is probably not as it's hard to get to the lower shaft because of the spring that hold the oil pump drive gear in place. I had one that was really stuck and I had to make a collet puller to get it out.

Thanks, Bob, for your idea about using a collet. Building upon this concept, I finally got the jammed distributor shaft out of the top of the oil pump drive gear assembly.

I tried almost everything without success, until I created a customized tool that not only easily pulled the shaft out, but it only took a few minutes to do so.

I started with a .500 caliber bullet puller collet that fit perfectly over the 1/2" diameter distributer shaft. I then slid a 1/2" x 3" galvanized pipe nipple over the collet. Then, using a 6" long 3/8-16 threaded rod with an appropriately sized nut and washer to pull the collet into the pipe nipple and clamp it tightly around the end of the distributor shaft, I connected the 3/8-16 threaded rod to a 5-pound slide hammer. I needed a couple of adapters to fit the 3/8-16 rod to the end of the 5/8-18 threads of the slide hammer, but after connecting everything together, it took only one blow of the hammer to pull the shaft right out. Finally! :D

Here's a picture of the "Rube Goldberg" tool I had to make to get the job done. It wasn't cheap, but it was worth not having to drop the oil pan.
 

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