Why? Going tubeless means you can't air down near as much for the times you need a wider traction patch. Get a set of the Motion Pro Bead Breaker irons, watch a few Youtube vids, practice at home. Once you have the hang of it things are fairly easy on the trail. Carry a patch kit and spare front tube (will work in the rear if needed). I carry a manual tire pump to conserve space. Also, strongly consider rim locks to help prevent sheared tube stems and if needed you can still ride it out without air. At a minimum a rear rim lock.
If you should bash a rim it may become unsealable if tubless, therefore, tubes are king. If you wanna go a safe route, look at Moose Racing for their system.
Far easier to install a gummy worm then pull the wheel and patch in the field. Without a center stand, it is a PITA to remove the wheel. That's the why.
I have never aired down. When off pavement I am mostly on fire roads and easy trails. I don't do single tracks. The main reason I ride the DR is to be able to do unpaved passes here in Colorado. And to be able to find camp sites off the main roads. Should I try airing down? That would be a good reason to stay with the tubes.
Second I can still carry a tube if all else fails. Simply remove the valve stem and install tube.
My 36hp DR650 (less at high altitude) had never spun a tire so I didn't think I needed rim locks.
Just wondering if anyone else on the forum has done it.
PS: Moose racing system sez not for the street.