That is interesting. I wasn't sure if that detail setting would affect this kind of map, but it's good to know in the future for troubleshooting purposes.
To enable screenshots, go to the display settings. There's an option to turn on the screenshot feature there. After turning it on, just tap the power button and you will snap a picture.
The nice thing about the Oregon and other new units is that there are no limits on the number of map files (except only one of the "custom maps"). You can load maps on the Oregon using Mapsource or Basecamp, just like your 60csx. This will create a file named gmapsupp.img in the Garmin folder on the Oregon (either internal memory or a card, depending on which you choose).
After loading your first map, open the Garmin folder on the GPS and rename the file something descriptive, but be sure to keep the .img file extension. For example, you could name the file GarminTopo.img. To play it safe, only use letters and numbers in the name and no blanks or other characters.
Now you can go back to Mapsource/basecamp and repeat the process if you want to add another map. Also a good idea to back up those files in a folder on your computer. That way, in the future you can just drag and drop the map files to manage them on the GPS. Pick filenames that will make it easy for you to remember what the maps are in the future.
I use GlobalMapper, but that is only because I already have it. Probably overkill to purchase for this purpose and there are several other nice programs for this - but as usual, they are for Windows and not the Mac. I have posted links to some of these here:
http://forums.gpsreview.net/viewtopic.php?t=15841
Also a lot of information in Garmin's own forum, with helpful people - including the software developers themselves:
https://forums.garmin.com/forumdisplay.php?f=205
If you want to make maps from the NJ 2007 orthoimagery, I would give some serious thought to getting a BirdsEye subscription instead. It is the same data but only at slightly lower resolution (~2 feet per pixel vs 1 foot per pixel). I posted comparisons in another thread; it looks very nice to me. It's a lot easier than making custom maps and there are no limits as to the size of the map. I put all of the pines plus a big chunk of upstate NJ on a 16GB memory card and have it available everywhere I want to go in this state.
You don't need to renew your subscription after the first year to continue using what you've downloaded. And when you register your Oregon, you get a coupon for a 10% discount, so it ends up costing $27. It's all done in Basecamp, which runs on the Mac. The program is a bit buggy, but still worth it.
If you plug your Oregon in and then run BaseCamp, it should ask if you want to use BirdsEye (have not tried on the Mac, but this is what happens on the PC). Just answer yes and it will get you started. The nice thing is that you don't need to purchase anything to download the imagery to your computer. That part is free, so you can see what you think. It will let you send a small sample - about one mile x one mile - to your GPS. If you decide to purchase, you can do it at any time. That will then allow you to unlock everything you've already downloaded for use on your GPS.
After you've had a chance to absorb some of this, send me an e-mail if you have specific software questions. Or post here if you think they will help others.