It looks like it's time for some work then. Or, time to spend some money. Make sure you read the TM on doing this. The wheel/tire is about 382 pounds and can hurt you.
Make sure the tire is completely deflated when beginning. When you first remove the CTIS wheel valve, look for differential lube exiting the hollow stud. If you find this, you will need to replace the hub seals. If the wheel valve has lube in it, it will need to be replaced or dismantled and cleaned. If the diaphragm is intact, you can re-use it. Rebuild parts are not available for the wheel valves so if the diaphragm is toast, the whole wheel valve is toast.
Make sure you thoroughly clean the groove where the o-ring goes. If rust is present in the groove, thoroughly clean with a wire brush and paint with spray paint. Don't reassemble until the paint is thoroughly curec. Do not use any sealant on the O-ring or grommet. You can use tire mounting lube on the interface between wheel and tire. Make sure also that you have the bead lock lined up properly so that the valve stem is not blocked. The nut on the valve stem should be torqued to 45-60 Lb-Ft. The nuts securing the wheel halves are torqued to a very high value and I can't remember the number, but the TM will tell you. After the wheel is remounted, try to minimize any movement of the valve stem while attaching the CTIS tubing. Oh, and be very careful not to damage the threads on the studs during dismount and remount.