I always thought it was strange that the Aramanthine Gate was the main entrance to the city, given that the description of the wilds paints it as almost completely inhospitable. Meaning that it would be unlikely for anyone but the most seasoned of wilderness survival experts to make any sort of journey across land. A large group in a caravan perhaps with lots of guards? But then there's the logistics to consider, namely the dense forests, not to mention hoisting up goods and such once you arrive at the base of the peaks.
Perhaps it would be better to have the main entrance thread for new PCs located at the docks, since arriving via ship sounds a lot more feasible and safe.
I mentioned this here rather than PM in case anyone else wanted to comment.