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That said, for a dungeon master it's much easier to do milestone leveling and have all the players be the same level. It's a lot less to keep up with, and certainly for writing adventures I think it takes a load off the DM if they only have to worry about writing it for 4-6 players of 3rd level, than 4-6 players of 2nd-5th level.
The wildly divergent capabilities of characters, however, was not one of them. In the presence of most GMs, having the weakest character meant a) dying, or b) not having anything to do. Neither of these is really conducive to enjoyment.
There are a handful of GMs I've met in my life who could give equal "screen time" to characters of wildly divergent capabilities, but those are few and far between.
Mixing levels amplifies this already-existing problem tenfold in my books. (Never mind that levels measure nothing meaningful in D&D; that's a rant for another day.) If you're the first level magic user in a group of 3-5th level other things, your entire gaming session consists of cowering in the corner and hoping you don't get noticed. You have nothing you can do that helps anybody (unless you're lucky enough to have gotten Sleep -- in which case you got to do one thing that might have slightly contributed), and this will also very badly impact your ability to level up to a point where you can be useful.
What she did was give each player that was there their 4 level 0 characters for the funnel. After that, we all picked a character to level to level 1. The idea would be that it took 1 game to get to level 1, 2 additional games to get to level 2, 3 games for level 3, etc.
If a player was to have their character die, they'd start again with either 4 level 0s or a level 1.
So figuring out when you level is easy, since you only have to count the number of games you were able to play in. But you would still eventuality get level differences, as players die or miss games (again, this was supposed to be for open play)"
I appreciate the comments about mixed level parties being difficult to adjudicate for. But one thing that is different for old school (unless I am mistaken they changed this in later editions) is that any magic user could use any scroll. Even if they are not high enough level to cast that spell. So if you have a low level wizard among your 5th level parties dropping a few scrolls changes the whole dynamic.
Provided you don't get instakilled by the first creature larger than a kitten that takes a swipe at you.
Provided you don't get BORED being relegated to the sideline for multiple grueling hours of watching OTHER PEOPLE have fun.
I mean my calculus is simple: I play games for fun. If I'm not having fun, I don't go to that game anymore. I don't plan fun on spec. It's fun out the door or I move on.
The non-combat things that hairylarry mentioned can ameliorate this, but in my experience those tended to be few and far between in most campaigns. You'd have a short time in the village talking to the villagers and then it's the next fifteen sessions in the dungeon.
There are a great many things to praise in the old school. The way mixed-level parties worked was not one of them. Some GMs could figure it out. Most couldn't, leaving the low-levelled character's player bored and/or frustrated and, very likely, absent next week.