It just so happens I just got back from the exact trip your describing. I went from Chicago to Estes Park to Moab to Ouray to Silverton and then a BIG detour through Gunninson to Crested Butt and then back to Chicago.
Everyone is different depending on how to "read" a map. I used the following maps and still got "lost"
1. The Books at funtreks.com by Charles A. Wells , I purchased Moab and Colorado
2. Stock Nuvi GPS
3. National Geographic Trails Illustrated Moab North, Moab South, Arches Park (excellant off-roading ) Canyonlands , and Durango Cortez, Telluride, Silverton, Ouray , Lake City.
In ALL the cities they have specialized maps just for the trails you want. I purchased the "Jeep Trails of the San Juans plus Historic Mining Towns"
You would purchase a ToPo map to see how HIGH you might be. If you have altitude sickness this can really help out and the terrain.
Most of the "trails" are marked at the beginning and at some cross-roads but sometimes you can get "lost" real quickly and get confused. A line on a map is totally different then the real thing.
I would also suggest to read about ALL the trails and then pick one or two for a day and have a game plan. Or you would just get over-whelmed with the possibilities. Also, some of the trails are "short" about 5-10 miles but it would take you a half a day to complete because you would be going about 5-10 mph and stop/look,etc..
If you have any other questions just PM me, I just got back. And, planning the trip again.
BTW, you gotta take highway 128 from Colorado coming into Moab.