While i like a lot of suggestions here, i cant help but wonder how suitable CoS is for introducing newbies to D&D. I guess ive always thought its a great adventure for old timers to give them a change of pace. Adding personal quests for each PC, I know you want that to help them stick together, but unless you know your players well (from experience) i really do wonder if you risk turning their focus to themselves not each other. A single shared objective is always the best and easiest way to make sure players mostly cooperate, and new players sure can benefit from being encouraged to cooperate from the get go. CoS is quite a lot of work to run even if you dont change too much, its comolicated for dm and players, and has so many ways for inexperienced players to get themselves killed. i guess i just fear that by changing so much, with new players, you might do too much prep work that never sees the light of day (so to speak).
Last thng, you say you have timid players... Again is CoS really what they will enjoy, or are you forcing something on them because you want different players? I dont know, but i think its a valid question. You want new players to have fun. When I ran CoS we had fun because it suited our collective tastes for bad taste, and failure was something my players were totally up for as an option. I could be wrong, but most new players probably just want to win, then they will come back for more and complexity can gradually unfold.
Last thng, you say you have timid players... Again is CoS really what they will enjoy, or are you forcing something on them because you want different players? I dont know, but i think its a valid question. You want new players to have fun. When I ran CoS we had fun because it suited our collective tastes for bad taste, and failure was something my players were totally up for as an option. I could be wrong, but most new players probably just want to win, then they will come back for more and complexity can gradually unfold.