How does one handle a siege-type battle?

So. Things suddenly got interesting for my game of apocalypse world, where I'm the MC. My Gunlugger has teamed up with my Hoarder to try and take over the Wastes. My Hocus has a "story" cult, and this isn't part of his plans, so he's doing everything in his power to advance his and his cult's "story" at any cost. The Gunlugger decided to go to this beautiful, gorgeous metropolis; the single gem in the damned wastes, a testament to humanity's survival at any cost, and a monument to the technology that got them there. This is where the question comes in....the Hocus has a plan involving the Hoarder, involving his cult. The Gunlugger blew up the city with a few bombs strategically placed and fucked shit up. The Hocus capitalized, rolled frenzy, whipped the survivors into a mob, and is now advancing on the Gunlugger with 200 angry, angry cyborgs. The Gunlugger also just recently took over the Hardholding (read: decapitated the hardholder with a chainsaw) and now has a 60-man gang at his disposal, in addition to the townspeople who are scared shitless of him. Things seem to be escalating to a magnificent, beautiful climax where the status quo is going to be violently ripped apart and thrown on it's head. My question here is: How. The hell. Do I manage that kind of battle? xD and forgiveness for the exposition, but I was quite proud of how everyone's story is going and I felt like it needed to be shared.

Don't manage the battle, deal with what the players say they're doing. Describe what the Hocus sees when he gets there and ask what he does. Play to find out what happens.

This is PvP right?  If the PCs are acting as "generals" then they might want (and might even deserve) a strategic view of the situation as it unfolds.  If you want to take the game there, you might consider a Custom Move both players could both use.  Something like...

Battle of the Hardhold
WHEN YOU COMMAND YOUR FORCES IN THE BATTLE OF THE HARDHOLD, Roll +Hard.  On a 10+ choose three from the list below.  On a 7-9, choose two.  On a 6 or less the enemy chooses one of your seized locations to destroy or hold.

[ ] seize two locations not already seized by your opponent
[ ] take a location from your opponent
[ ] destroy a location with enemy believed inside
[ ] avoid taking damage
[ ] avoid killing civilians
[ ] avoid destroying resources

A "location" might be something like The Armory, The Infirmary, The Storage Vault, The Kitchen, The Parking Lot, etc.

The players may choose not to do this, of course, and may simply do one of their own moves.  Resolve everything simultaneously.  If anyone fails a roll of any kind, you might use items from the above list as Hard Moves (i.e., you are playing the other player's NPCs for a moment).

After the players call their moves and you resolve them, use the Gang Harm Rules to determine overall damage to each side.  Maybe the side with more seized locations gets 1-armor against harm coming in.

I would run this using the optional Battle Moves, with most of the involved players fighting with gangs as weapons.  The joy of the battle moves is that you can run the timescale as anything you want (each tick being moments or hours).  It will help if you have maps of the city with important objectives labeled.  It's even better if possession of key locations confers some advantage or effect (like possession of The Spire allows you a bonus when firing down on enemies in adjacent precincts, or possession of the Tunnel Complex lets your side Go Aggro anywhere in the city as you strike by surprise by boiling out of hidden tunnels).

Whatever you do, make it suitably epic.  :)

My opinion, alternate between perspectives. Building on Munin's point, get a map of the city, and divide up the key strongholds. What kind of character does each place have and why? That makes this less like a numbers game, more like a narrative epic. Is this entirely one sided? Is there internal conflict within the players' ranks? I wouldn't stick hard and fast to any particular type of rule (although the ones suggested are good) but change according to the situation. Most of all, the battle is going to have a character, inevitably and I'd guess you'd let the players determine that but there's no harm in pushing them there a little in my opinion.

Examples of battle character?

• Skirmishes
• All out total war
• A mixture of the above
• Blitz warfare
• Seige

I know your OP talks about seige-type battles but that might hem in the roleplay to a certain type of fight and also limit you from switching perspectives and scales in terms of time/space/whatever. Hope this helps!

as always you guys are awesome on these forums. thank you again, these are all magnificent suggestions