Great post on going tubeless. I disagree on one point. It does not matter if the front rim is designed to be tubeless or not. If you get a flat with a tube, the air will escape much quicker than if the spokes are sealed and there is no tube. either way if you let the tire go all the way flat, the tire will still come off the rim. If you pick up a nail while tubeless, deflation will be slow enough to give you time to stop and repair the leak before total deflation. I have Goop sealed the front and rear wheels on my 1998 Tiger several years ago and only the rear wheel has a tubeless style rim.
In addition to keeping a string type plug kit, also keep a DC powered air pump on the bike. (I saw a compact one recently for sale at AutoZone in the Slime display. CO2 tubes are a waste of time.
1998 Triumph Tiger