If you can forget about geocaching for a day or two, you may have better luck with your connections.
1) The first time a Delorme PN-xx device is connected to a new computer, Windows needs to download a new driver for the computer. Presumably that has already happened, but it wouldn't hurt to plug the device into both computers in sequence while connected to the Internet w/Windows Explorer active to see what happens. if you are using computers, such as Macs, and not basic Windows PCs, let the other forum members know.
2) Then become at least a little bit familiar with Topo9. Create a few Routes under the Route Tab and create a few Waypoints under the Draw Tab. If you need help, click on the yellow question mark
under the applicable Tab to be taken to the appropriate page on the Delorme User Guide. If necessary, search further in the User Guide search window, as you cannot turn the pages! (PDF version with page by page readibility is available on Delorme.com for download).
3) With the PN-60 unplugged and powered down, and after creating a few routes and a few waypoints, Click on the Handheld Export tab and select Synch. Wait a minute for the computer to find "nothing".
4) Plug in the PN-60. Press the PN-60 power button.
5) If all goes well, press the Synch button (twice to be sure if necessary) to see if your routes and waypoints are transferred.
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If that works, the geocachers will get you the rest of the way with the plug-in "easy" instructions. As for me as a geocacher for test purposes only, I find it more convenient to receive a PQ in email, unzip it, and import Geocaches (really just special waypoints) into Topo9 using file import on the right side under the Draw Tab>File button.
6) Then Synch (Send) the geocache file to the PN-60 and all the files are more likely to stay in synch with each other than messing around with the "easy plugin methods".
Just my 2 cents worth on loading geocaches. Good luck.