I have asked a very similar question to yours, and I'm pretty new to the hobby. There's a thread called "Unfamilar General" (within the NC general discussion banner) - check it out. I've come to agree with what that Bums have put out - the Cuban legacy brands aren't worth the MSRP compared to non-legacy brands such as Tatuaje and Room 101. I haven't ventured far in to the NC legacy stuff such as H. Upmann, Partagas, Cohiba, but I have had some I like, but not for the MSRP. You can definitely get a lot of these legacy brands for much cheaper than MSRP, but to me, there's much more interesting things to check out (at least to me). Check out Cigarbid, and the major online retailers for heavily discounted legacy brands. Part of the fun I'm having with being a Bum and the hobby in general are exploring what's out there.

I'd recommend these if you want to stick to legacy:

RyJ Reserva Real Nicaragua (blue band and reviewed by me)

H. Upmann by AJ Fernandez and Jose Mendez

Partagas 1875 Clasico (can score cheap off cigarbid and was review by me)