kyocera 7135 handheld/Outlook hotsync issues

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I'm having a heck of a time getting this to work. The City Treasurer has a kyocera 7135 handhead that's supposed to hotsync with Outlook. I upgraded his computer recently and put together all the files and links he had on the old one. Everything's up to snuff except this feature. The phone sits in a modem/cradle that attaches to his pc over a serial link using COM 1. I was getting one of the common errors of "This feature is not available when port is in use" but worked with tech support to solve it.

New problem. Although the vast majority of data is sync-ing ok, there are some problem areas. He says he used to have two contact files on the phone...city directory and contacts (meaning everyone else). He only has part of the city directory on the phone and doesn't think he has the other directory there at all.

I checked Outlook, went into folder view, opened up his personal folders and noticed that all the folders he has in the main Outlook folder are duplicated in his personal folders...sort of. There's a slight difference in the contents of each. I have been learning about kyocera wireless and synchronization pretty much on the fly and have reached the limit of my ability to deal with this. Help.