[quote=@Unraveller]
New thought, you know having one big group of undead roaming around sure seems like it would be strange or make the setting easy. Unless of course there were far more creatures lurking behind ever corner. Though that could make combat more repetitious. I feel splitting groups up would be logical, though GMing for two or more different groups at the same time could become confusing. What about some people staying at the shrine in order to rest or something to that effect? Just some thoughts, though I could be completely inept at this subject.
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I am hoping that if we do end up going through this in a group, we'll be forced to separate anyways. Like, I don't want the progression of the roleplay to be similar to that of the game in that there is really only 1 path to take with shortcuts to activate along the way.

If anything I want our characters to come to crossroads and have to separate. For example, in the Undead Burg; which might possibly be our characters first destination, we should assume that as an Undead Township there are many different places for us to explore. So we might split into two groups. Because of this, one group may end up at the Sunlight Altar, and the other may end up at the place where the Capra Demon boss fight would be (Although I am thinking of changing that boss into something different, if you have any ideas then feel free to share).

In terms of adding enemies, I think we should just consider enemies to be more threatening than they were in the game. In the game those hollows might not be a problem, but those are hollows of relatively skilled guardsmen and warriors in the Undead Burg; in a roleplay context I assume even they would pose a threat to us. Different types of enemies can also exist in the Undead Burg if we want them to. It's fairly close to the Depths so it might not be a stretch to say that a few butchers are lingering about.

In the end it'll be up to each individual roleplayer when it comes to who we face and how they decide to go about facing it.