After playing around for a while with 2006 HH, my wife and I figured it all out. I can now sucessfully take a .GPX from geocaching.com and change it to waypoints that delorme can use.
1) get the GPX file
2) change it to a compatible format here: http://www.gpsvisualizer.com/gpsbabel/ you want to choose gpx input to delorme handheld output.
3) copy/paste the code at the end of this post into a file called "convert.vbs"
4) copy your converted file from step 2 into its own directory (trust me on this) with convert.vbs
5) run convert.vbs. it will ask for the name of the converted file.
6) after its run, you'll have a file for each entry in the converted file. so if you have 200 entries in your GPX, you'll have 200 little waypoint files. copy those into your "my documents" on the handheld device. when you open up delorme, you'll have all your waypoints loaded!
you can manage the waypoint files however you want. i keep different batches based on the GPX file. an example would be is I keep the 44143 zip code 15 mi radius GPX file in a directory with all of the extracted waypoint files.. I have a seperate directory for my 44134 15 mi GPX and waypoints.
I hope this makes some sense. delmore isnt *that* bad as a tracking tool for geocaches, just takes some persuasion
Dim objFileSystem, objOutputFile
Dim strOutputFile
Dim kitty, chinchilla, fish1
dog = InputBox("Filename?")
strInputFile = "./" & dog
Set objFSO = CreateObject("Scripting.FileSystemObject")
Set objTextFile = objFSO.OpenTextFile (strInputFile, 1)
kitty = 1
Do Until objTextFile.AtEndOfStream
chinchilla = objTextFile.Readline
fish2 = InStr(chinchilla,"::")
fish2= fish2 - 1
fish1 = Left(chinchilla,fish2)
Set objFileSystem = CreateObject("Scripting.fileSystemObject")
Set objOutputFile = objFileSystem.CreateTextFile(Right(fish1,6) & ".wpt", TRUE)
objOutputFile.WriteLine(chinchilla)
objOutputFile.CloseSet objFileSystem = Nothing
kitty = kitty + 1
Loop
WScript.Quit(0)