I like what Orp says. I do think we need to sort of limit the amount of items you start with, as long as we can be flexible on what constitutes and "item." A sword, a bow, chest OR leg armor, etc, rather than specific pieces for each body part. That will simplify the starting process and encourage people to buy stuff because they want to.
Also, we make it clear that we're flexible on what kinds of items new players can buy. If a new player wants to buy, say, a bandanna, or an eyepatch, or whatever for his character because it fits him, and none of the stores have one listed, he should be able to buy one from an appropriate store anyways by going in and asking for one.
That ties in with the general store thing that Gray posted earlier.
Of all the graveyards in all the towns in all the world, she had to walk into mine.