MDYoungBuck, since I can't remote into your GPS to see what you're seeing I can't say with certanty. But if you bring up the East or West CD on you PC, set "change map scale" to 15-20 miles to start with to the general area you want to select.
Then select "map tool" option on the tool bar (the buttonlooks a little like the state of Minnesota" or "Tools" > "Map" on the menu at top. Then start selecting the areas (which turn pink). Then set "map detail" to the "highest". Click the "hand tool" that then take you out of "map tool" mode.
Now you can zoom in and look for details, set waypoint, routes, and save the map set as whatever name makes sense.
Finally, from "Transfer" > "send to device" option with your cable to your GPS already hooked up, upload the map set. Note that any other mapset is replaced. So, you'll only have detail that you can zoom into on your GPS in the areas you chose and sent to the GPS. You can alway create other map sets and upload those at other times.
It may also be that you need to play with the zoom in or out on the GPS to get the level of detail and perspective of the area. You have to get into less than 1 mile perspective on the zoom to see all the detail from the topo map.
I do agree the $100 cost may seem sort of high. But if you can get it to work for you and it gets you in and out of back country safely just once, it worth that to me. We did use this on my GPS this fall hunting 5 miles off the nearest dirt road over many ridges and draws when the sun started going down. We knew the general direction to follow by compass, but the "bread crumb" trail on my GPS kept us on the right tract after dark up the right ridge to get back to the truck. I definitely like having it then! Of course that trail feature is part of the GPS out of the box. But we've used it to find (approximate) BLM / private boundaries and such, too.