I haven't heard of anyone having problems lately (last 5 years). It is clearly USFS property and gets a LOT of visitation.
Randy...were you there Sat night? I group I know was there that night then did Marengo New Discovery Sunday
Yes, there was a camp set up right at the main Messmore Overlook, and for that reason I moved further down the cliff a ways to rig. Looked like some young guys in a full-size Dodge Diesel pickup and also a smaller red pickup. I was mighty impressed that they were able to navigate the road actually! I never did talk to them. Now that you mention their cave trip, I wish I would've.
Concerning the private property issue: The county "road" that ya hike in on has a cable strung across it 0.1 miles past the main Messmore overlook. That's where the "No Trespassing" signs start. The road beyond Messmore, however, is now very overgrown, which is new to me. The guy seems to have his property pretty well marked out on the Messmore side. I found (and marked on my GPS) nine property markers, and I'm sure I missed some!
Also, since there has been mention of caves and WNS, which has nothing to do with Messmore Cliff, I'll mention something else. I'm guessing these folks are referring to an area that can be found if you drop down the hillside directly on the opposite side of the county road from Messmore. If you drop about 80 yards (I'm getting these distances from measuring between my coordinates that I imported to Google Earth) straight down the hill perpendicular to the county road and then begin contouring the hill to your left (in a northeast direction), you'll find some neat small cliffs/shelters and even an arch called Aarowhead Arch. But you have only about 150-175 yards to contour the hillside for cool stuff before you run into private property. And unfortunately, I'm certain that there's some cool stuff on the other side of the No Trespassing signs...and maybe an old mad camouflaged like Rambo.
I'm sure this is the rock shelters and arch referred to in Grandpa Caver's link that he provided in his first post on this thread. Indians apparently used to inhabit the area and in some way or another utilized some of the natural shelters. I think I recall a sign at one of the neat areas indicating this. Papoose Cave is also down there but appears to be most likely on private property (I may be wrong on this, but it's sure close to the property line!). Anyway, the area is definitely a nice (and short) bit of exploration to add to a day of climbing at Messmore, but just be alert for the No Trespassing signs.
Now that you mention that story of being run off at gunpoint, I remember hearing of that happening to someone before. Concerning this old fart (if he's even still around), His little "vacation" shack is located at N38°17'20.50" W86°31'34.98", and as I mentioned is clearly visible on Google Earth. As a crow flies, it's 0.25 mile from the Messmore Cliff. From there you can see a road that heads down the hill away from Messmore (opposite from the direction you hike in from) that leads down to Old Felker Rd (Co Rd 128), right across from a farmhouse. Maybe he lives there???
So I'm pretty darn certain that the guy probably rarely entered on the county road that we would enter on. And perhaps that's why hardly anyone that you run into has actually seen the guy. Beats me.