First, regarding the tires. I've known guys who have sealed off their spokes on the inside of the rim and were able to run tubeless tires. I don't actually know if anyone makes a tubeless tire that will fit the TW since most tubless tires require a minimum of 27 psi to keep the bead seated on the rim.
I didn't know that there was a headlight switch on the TW. However, you may have just disconnected the high beam or low beam so when the hi-lo selector switch is moved, the disconnected one doesn't light up. That should cause you no issues since you are going to offroad only. Just make sure the disconnected wire is not able to ground out to anything. Maybe tape it up with electrical tape.
I didn't know that there was a headlight switch on the TW. However, you may have just disconnected the high beam or low beam so when the hi-lo selector switch is moved, the disconnected one doesn't light up. That should cause you no issues since you are going to offroad only. Just make sure the disconnected wire is not able to ground out to anything. Maybe tape it up with electrical tape.