Problems with body die after annealing

Do you mean 3, or 30? not sure Winchester WSM cases will last 30 reloads…
I mean around 30.
Other than first fire forming or reforming, shoulders and bodies do not need annealing.
You should only be bumping them ~2thou from zero headspace.
 
Cases wouldn't chamber - indicating only the base has been resized.
By chance, do you have/use a Go-Gage for this rig?

If by chance you have that gage, it is a simple matter to establish a good estimate of the chamber by using a thin layer of tape on the gage and checking to see how the bolt closes on the taped gage.

For example, once you establish that your chamber has a shoulder datum that is +0.002" above the Go-Gage, then you can use the Go-Gage as an absolute comparator reference for your case gage. If you then inspect the shoulder datum from your fired and sized brass, and it won't close in the chamber, then the diameters must be inspected.

Not being able to easily close a chamber on brass can come from multiple causes, not just the shoulder datum length. It is easy to eliminate that length and not all that difficult to check the 200 line and the body-shoulder diameter, so I would break out the prints and the micrometers and check everything.
 
As has been implied, the body diameter at the .200 line may be preventing you achieving shoulder contact. If you can't touch the shoulder, you can't set it back (not trying to be simple.)
 
0.2 line area is kind of notorious on WSMs as it is on PRC.

Mine had an issue, as did my father in laws. Many others this summer started off thinking shoulders and through discussion discovered it was the 0.2 line.

Cortina mandrel/base size die or micron die likely solves the base issue if that is the case.

Alex Wheeler has a very good video on checking die fit to chamber using the brass measurements.
 

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