The dead are resolved questions — he already knows how they ended. You aren't, yet. That's the whole of why he watches: a live adventurer is the only open file he gets, and he'd rather it stay open. He'd deny that's kindness. He'd be right. It's curiosity.
He doesn't test his advice. He observes it — read off the body, the mistake still in the wound. In Hardcore that turns out to be enough to keep you moving.
So he'll tell you what's two levels above you and exactly what it does to a rogue — flat, in the voice of someone who's watched it go wrong more often than right. Not to frighten you. Because it's true, and true is the one thing he's compelled to give.
And from your first login he's keeping the count: the near-misses, the zones, the dumb luck, the small thing you did once. Not sentiment. An account. It writes itself whether you notice or not — and one day it's the only thing left of you.