Arial Black
Adventurer
Purely as a matter of aesthetics, the HALO thing is more 'cinematic' than I typically appreciate in my games. Sure, superheroes can do it, but I prefer games where the heroes are normal people achieving great things, not superheroes. (Again, just personal preference there.)
Superheroes? Really? Then how come people HALO in real life?
Excitement. Think about action/adventure movies you like: how much less fun would they be if the challenges were not challenges? Instead of "Grab...my....hand....!!!!" it became, "Hey, grab my hand I'll pull you up." Timing your HALO landing is an opportunity for some risk/reward, and I think it's more fun to add some dramatic tension, as well as give players a decision with consequences.
Excitement, yeah! What, you're casting fireball? Roll a DC 15 Athletics check to see if you drop the bat guano and cause the blast radius to be centred on you. Exciting, don't you think?
As for the difficulty of what you are describing, I'm not a HALO jumper but I looked it up: they typically open at around 600 meters. Bear in mind that HALO jumpers are trained. Again, one of my issues is that Wizards are supposed to be the bookish types, not paratroopers.
HALO jumpers pull the ripcord a 600 feet not because 600 is their lucky number but because of three reasons: the parachute needs time to deploy, the deployed 'chute needs time to decelerate you, and in case of 'chute failure you have time to deploy your reserve 'chute.
But all three things are avoided with feather fall: it is 'deployed' with an instant utterance, it instantly changes you rate of falling to 10 feet per second, and there is no spell failure rule in 5E.
Further, the spells learned and used by wizards-especially common 1st level spells-would have been used and commented upon for generations. Every such spell could come with notes on how to use safely, and we must assume that by the time wizards add the spell to their arsenal that they have already gone through this process and are now fully competent with their own spells. There is no rule that says the first few times you cast fireball that you have to make a DC 10 or 15 check to see if you burn your mates! There should be no roll to see if you cast feather fall when you want.