I recently tried to install the Magellan DataSend tool to talk to my GPS, and it almost works. However, I did find one funny with it - the program did not "see" the COM ports until I added the following entries into the registry:
[HKEY_LOCAL_MACHINE\hardware\devicemap\serialcomm] "COM2"="COM2" "COM1"="COM1"
(these were found via a file on the Magellan install CD named win95com.reg).
Perhaps these should be added to the Wine registry?
Once added, then the program would run - at least right up to the point where I told it to download the data to the GPS, at which point it threw and exception and died.