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My son (now 13) has been my primary opponent since he was a kid. I'm not ashamed (well, just a little) to admit that he regularly cleans the floor with me. Our primary games are Frostgrave and Deadzone.

He also has a vivid imagination, and it constantly coming up with really wild ideas for campaign settings, monsters, magic items and so forth. His latest kick is more powerful fighters who can gain experience and feats, almost like D&D characters. For example, he spent an hour last night telling me about The Hunter, who can attack a second time if he wounds his opponent on his first attack, gets a trick shot that ignores terrain, and can set explosive traps. He wants to plug said fighters into Frostgrave, but I'm not sure that wouldn't break the game, or at least warp it into unrecognizability.

So I put it to you, dear reader. I need a skirmish-level game or games that center on customizable, upgradable characters for a (slightly-bloodthirsty) middle schooler. Ideas?

A Song of Blades and Heroes is the go to game for this type of customization.

You may also want to think about some sort of co-op dungeon delving game too. Heroquest is a great start and you can easily add all sorts of content into that. I recall doing that myself as a youngster.

If you want a huge base of customisation like that, you may find a RPG system works for what you want.
D&D isn’t too hard to manage a few characters a side when you’re running as a pure combat game. And can even have wild dragon encounters that randomly cause havoc!

The white wolf system for world of darkness also can be quite good for combat if you come up with some missions that use the other stats.
Which it sounds like your son may enjoy, and it has a dark ages setting.

Just depends how much you want to put into each game.

Inquisitor from games workshop is a good skirmish game if you put in the effort as well, but it can be a bit daunting if not ready to commit. But is almost a RPG hiding under a skirmish game coat.

Zona Alfa might work, your whole crew gains experience, improves stats, earns money (hopefully enough to retire) and can buy upgrades to kit/weapons. They also die and you need to recruit new members.

The setting can be transported to any modern time and location, which means that you can make an Exclusion Zone in your own town if you like as you fight of mutants, zombies, bandits and other crews whilst trying to retrieve enough weird salvage to pay for the grenades you used up acquiring it.

Good fun, narrative driven and adaptable gaming.