Are we talking about a road bike, where you might go 50 miles from home? I tried tubeless... specifically Pirelli PZero 700x25c tires on Fulcrum Racing3 2-way wheels. What an expensive mistake!
IMHO, for tubeless to make any sense at all you need wider tires and also wider wheels than I've got. Much wider.
Apparently all "bacon" repair plugs aren't equal - the Lezayne variety didn't well work for me! If you're gonna rely on bacon plugs, you should probably practice using them at home before trying them along a roadside. Once plugged, you should plan on installing a brand new tire at the first opportunity because riding at road speeds on a plugged tire is a very bad idea. Note: if the plug is in the part of the tire that contacts the road,
you'll hear and feel a bump on every tire rotation. That's the road, trying to pull the plug out. Come to think of it... you should probably avoid turns.
You should certainly plan on carrying a spare tube, plus shop towels because you're gonna be a sticky mess when you install them. It won't be a quick job.
venomx... I think a different set of wheels might be a good investment for you, so that you can swap tires/tubes independently and much more easily.