Anor Londo (Duke's Archives) can be tricky, you also can't warp out so if you do get frustrated there's no way pick one of the other paths first. It isn't particularly difficult, but a lot of people tend to get lost at some point. Pretty easy boss.
New Londo Ruins is probably the easiest area. I had purchased a few Transient Curses before I tackled this area, I didn't end up needing them but I would suggest buying a couple from the female undead merchant in Undead Burg's aqueduct just in-case. One of the harder bosses in the game, though there is a strategy that makes the fight unsatisfying easy.
Demon Ruins (Lost Izalith) is pretty easy, just bring a lot of arrows. Easy boss.
Tomb of the Giants (Area after Pinwheel in the Catacombs) is really, really annoying. There is a helmet you can pick up in Lost Izalith (Sunlight Maggot) that will help, and I strongly recommend getting it before going here. Easy boss, if you've got a Divine weapon or some decent magic.
In terms of difficulty for the areas, in my opinion: Tomb of the Giants > Duke's Archives > New Londo Ruins > Lost Izalith
In terms of difficulty for the bosses, in my opinion: New Londo Ruins boss (legitmate) > Duke's Archives boss > Tomb of the Giants boss > Lost Izalith boss > New Londo Ruins boss (cheese strat).
I didn't find any of these bosses as difficult as I did Ornstein and Smough, however.
Pick which sounds best for you. I would really recommend Lost Izalith before Tomb of the Giants though, that helm will do a lot.
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