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It depends on what the new version looks like. Generally, I tend to prefer newer sculpts if they update size and proportions. After having built 20ish crisis suits since their initial release, the Tau commander kit was a revelation. Proportions, poseability, size - it was the perfect kit and still kinda is to me.

Generally speaking? No.

If I’ve an existing collection, I’ll use that. But if it’s a new army? I’ll use whatever is Off The Peg currently.

I don’t think I’ve ever upgraded.

90% of the time, no I'm not compelled. However, there are some times when I am.

1.Super Massive Scale Change. Am I still okay with 3rd edition Marines? Yep. Metal Avatar? Yep. Metal Grazgul? Yeah, that one is pushing it.

2. Total weapon layout change. Yes, some special characters are no longer the same weapons/wargear they've had in the past. Tau Commander Shadow Sun is the best example.

3. An extremely derpy model from the past gets a super massive Glow Up. We can all agree that there have been models that are just an assault on our eyes. If they get redone and actually look GOOD, I feel compelled to upgrade.

The Previously Mentioned Necron Destroyers? The old metal lounge chairs of doom? I still have them, still love them. However I now run them as Tomb Blades, as they look more like the official Tomb Blades than the current Destroyers.