Mine were removed without breaking, and I have had no leaks.

 

Yes, A-piller trim pieces often break during removal due to age of plastic, clip design or rough handling. My LH side is broken for unknown reasons and increases wind noise but doesn't cause moisture leaks. I'll avoid a WS R&R if possible due to possible leaks. Just be aware of that, monitor and if they do occur some additional sealant should take care of it.
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Yup and they are about 80 bucks a side according to the quote I got.
When the screen on my classic got replaced, it did leak. Safelite fixed it, but it was another half day being inconvenienced while they addressed the problem they should have done right the first time.

 

DIY WS replacements are not much fun but could be an option for those with the time/patience to do it right and care. Been there, done that and hope not in my future. May not prevent broken plastic pieces and $ savings might not be much if any after supplies/tools. Glass companies do quick/dirty convenient replacements at a reasonable cost so there's little incentive for most to DIY.
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If the company replacing the windshield breaks the A-pillar or any other trim why isn't it up to them to replace it?

 

update on this. Statfearm clarified my policy. They'll replace the screen with factory glass and no impact on my rate for $500.

I still need to pull the fender and snorkel to get it done, and i'll do it in conjunction with gluing down my dash, so will probably wait until late spring.