There are a host of sites on the web with tips on patching and changing mc tires. Go to
http://www.horizonsunlimited.com/Links.htm#TechnicalTips for a listing.
Comments - I carry 3 tire irons, 2 of them the original BMW irons which are excellent, plus one more slightly shorter but with a 90 deg bend on the end and a notch to hook it onto a spoke to act as a 3rd hand - very useful.
This should be all you need. Don't let anyone talk you into the foot long irons - if you need that much length you are DOING IT WRONG! Read the stories to learn the tricks. Adding a little air as mentioned above is much better than fully deflated, but I pull the valve core right out, and then the tube can find it's own shape (round and fat

and doesn't resist in any way. Much easier. (I've done literally thousands, and practiced for ISDT events).
Tubeless can indeed be run at pressures low enough to be useful. Mainly because they absolutely do NOT want to break the bead, which is the whole point of their design.
The difficulty in breaking the bead is the major safety aspect for motorcycles. These tyres do not break the bead when you have a sudden flat at speed - keeping the tire on the rim is a huge benefit! BTDT - a nail in the back tire high in the Andes, fully loaded, touring with passenger, 70+mph, 1000 foot drop, no rails nada, sideways as the tire rolled right off the bead and folded under, punching the nail right through the sidewall half an inch from the rim. Super scary. And the final decider for me. Tubed is out for serious loaded touring.
I am now converting my tubed G/S to tubeless for above safety reasons. Note that you can run tubes in a tubeless tire, (my tire of choice for the rear has been a Metzeler or Continental tubeless for the last 15 years) and I will carry tubes just in case I can't use a plug to patch the tire. Safety will be improved even with a tube in, simply because the tire doesn't want to roll of the bead.
Trivia - When tubeless tires first came out, the new design was - and still may be - called a "safety rim".
Getting tubeless tires off can be very hard, yes, but you have to do it less often. A c-clamp can be carried that will break the bead easily. From there it's no different. And a plug can be stuck in in minutes, whereas patching a tube is at least a half hour by the time you unload and pull the wheel etc.
Do NOT run one tube inside another. The cut edge of the outer tube will eventually chafe right through the "good" tube. I have seen incredibly minor damage inside a tire chafe through a tube in a hundred miles. BTDT. In Colombia... ended up patching the tire and tube just to protect the tube. Note that patches have very gently tapered edges to prevent the patch chafing the tire, so the reverse works!
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Grant Johnson
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at:
www.HorizonsUnlimited.com