1. I've never had much trouble with navigation although the ridges on the Cobberas can be a little misleading in fog. There are billions of brumby pads in that area and they don't always go where you think they should. Map, compass and plenty of clear thinking should be sufficient.
2. Native Dog has a good camping area and plenty of spare ground to leave a vehicle. There is also parking a bit further along near the start of the Playground 4WD track, or the Cowombat Flat carpark. Limestone/Black Mountain Road is 2wdable but some bits of it can be a little rough, so drive carefully.
3. There's reliable water in Indi & Pilot Creeks at Cowombat Flat, from Tin Mine and Dales Creeks further north, from Native Dog Creek at the campground and the Playground, plus smaller streams and pools on the Cobberas and the side of the Pilot. If you're concerned it wouldn't hurt to treat the water especially from lower down, although I've never had trouble with it.
4. Ignore the buggers. No-one is going to hunt you down and try to charge you for pitching a tent up there, except maybe at the official campground at Native Dog.
5. It should be on your map. Between the Rams Horn Track and Native Dog, there's a 4WD track that runs northish in between the Cobberas and the Rams Head Range, and eventually runs down over the Suggan Buggan River and joins with the Ingegoodbee and associated tracks. At the southern end it leads past an extended series of open meadows below the Cobberas. There's a campsite at the southern end of the main bit of open ground. The Playground is generally considered to be the area from there until you hit the road again at the northern end of the meadows. It's a great way to access the Cobberas.
6. The Playground can be a bit damp underfoot, but not really boggy. Scrub is occasionally a little awkward - usually worst at the creek sides - but the aforementioned brumby pads make the walking much easier. Just pick and chose which ones you use.
Route I'd choose is to go in via the Playground - and there's no reason you can't start by climbing the Rams Horn and then dropping down to the 4wd track - climb up to the main Cobberas ridge from there (find a pad just north of where the creek comes down from the saddle), go over Cobberas No1, out to Middle
and Cleft, backtrack and pick up a decent pad that leads towards Moscow (there's good camping on the ridge, the terraces, and a small flat with pools about halfway across), sidetrip up Moscow (best not to try to descend north from the summit towards Cobberas No 2 as there are several awkward sections of cliffy things in the way), over Cobberas No 2 (good camping on terraces and at the saddle between its two highpoints although water can be scarce there), and descend via Mountain Trout Creek to Cowombat Flat (again, great camping on terraces and at the Flat itself). I've done that minus the Rams Horn in one very long day but it would be better to take more time particularly if you don't know the area.
From there, to Forest Hill and up the ridge to the Pilot, down via Little Pilot, and either track or direct to Tin Mine Creek (great camping). Again, there are good brumby pads leading out to the viewpoint for Tim Mine Falls and it's worth a visit. You can pick up the track and go south along Cowombat Ridge, or make the steep crossing down to and then back up from Dales Creek before heading south to pick up the track. Scrub and treefalls can be an issue on the western side of Dales, and the ground is very loose in places so take care if you pick that option. The creek itself is very hard going and there's an unmapped waterfall at one point that has to be sidestepped, so I wouldn't advise trying to follow it.
From the Pilot/Cowombat Ridge saddle the easiest route is the AAWT, or at least to more or less parallel it along Cowombat Ridge back to Cowombat Flat. You also have the option of dropping down further to the west and crossing the Murray and using the Limestone Creek Track to return south. Scrub is a bit thicker here but still not that bad if you pick and choose amongst the brumby pads.
Of course, you can do that bit in either direction. In fact, probably easier to go via Cowombat Ridge and down via the Pilot. And again, good camping on the ridge and on the Pilot although you'd need to carry water up.
I've done an easy four day figure eight here, starting at the Playground, using the above route into Cowombat Flat, then up along Cowombat Ridge right to the northern end, down into Dales Creek with an abortive attempt to follow the creek all the way back to the saddle (which is how I know about the waterfall
), up to the Falls lookout, Tin Mine Creek, Little Pilot, Pilot, then a cruise out along the Cowombat Track to cut back over to the Playground from near Buley Creek.
Hope you have good weather. It's a fantastic area.