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ODST (you can skip missions super easily, aside from Coastal)
3
CE (If Keyes' "Flood bump" skip didn't exist, it would be below 2)
2 (it has its infuriatingly hard parts, but otherwise pretty much smooth-sailing)
Reach
4
with no exploits
if you exploit and use lots of skulls the list is probably different
4, 3, 1, 2, Reach.
However 2 and Reach are hardest due to bad design. Tip: When you get to the Space mission in Reach ignore the crys for help by allies since they are invincible.
other then that reach is definetly easier everywhere then h2 and ce (except in ce you can 1 shot hunters to the back with a magnum.... LOL)
when in h2 the snipers are op (once you know there location not as bad a problem anymore) , but then there is still the berserking brutes...
or CE's missions where you free keyes on the corvette, the library, the actual mission called keyes and the pillar of autumns engine room... those are hard by design in comparrison not just because the AI now runs at twice the tick rate or more
Halo 2 is probably the most unforgiving and with fastest player ttk. Reach just has some pretty miserable segments but its a lot easier to run through most missions, its mostly the last level thats really hard.
Halo 1 is close to 2 for me just because of Two Betrayals which is truly pain for me. Halo 4 is just kinda trash and it's just a lot of spamming forerunner weapons behind cover to clear rooms, with knights frequently nothing personal kid'ing you. It's the least fun of the legendary runs.