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The pricing seems schizophrenic? Some are half off, others are cheaper to buy from my FLGS at 20% off.

Do you think they will update them if a new version comes out or will I need to re-buy?

I believe you will need to rebuy. Just look at the Stormcast Eternals. It replaces the previous book and I haven't seen anyone say that their older book got updated for free.

So depending on what is on sale, they can already be outdated if it's not the new Stormcast book.

 shakespear wrote:
The pricing seems schizophrenic? Some are half off, others are cheaper to buy from my FLGS at 20% off.

Do you think they will update them if a new version comes out or will I need to re-buy?

They absolutely will not update them when new versions come out. Period. That said you'll be saving 20-30$ per book over buying the paper copies of new editions.