Would Classic or SoD be more friendly for a casual player wanting to eventually grab some gear in Naxx-40?

Everything you said in your post makes me think you’d really resonate with us in Legacy on the Grobbulus server. It’s a very solo leveling experience (we’re the only guild on the alliance, one guild per faction) but we raid Naxx and all other content in the game in a very casual / communal / fun / still get stuff done kind of way. This would be on Classic Era which I’d recommend over SoD for what you’re looking for regardless!

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