A dynamic, living OSR megadungeon will be my next campaign!

Sometimes things just fall into place.

Having received The Black Hack for Christmas, and enjoyed reading through it, I have had a yearning for doing something old school; a hex crawl, or a megadungeon, or the like.

Along came an excellent series of megadungeon posts at Hobgoblinry (two, three, four, five...) referencing a thought provoking post from Lich Van Winkle on the application of wandering monsters and my fate is sealed. A megadungeon it is.

But not any megadungeon.  I want to take my current experiments with dynamic planning and reusability forward, and work in some ideas I have been having about procedural mapping (note to self: I had better get those down first!)

Image (cc) Noicem

I want structured delving mechanisms, I want the thrill of old school dungeon diving, and I want to embrace what I have learnt from the new school of TTRPGs and my own evolving DM style.

I have a couple of other things on my table for January, so I'm writing myself these key questions in the hope the answers will percolate out:

How do I gamify the act of delving and what (if anything) can I add from the OSR generally to The Black Hack's rules for the likes of dwindling supplies and fear of the dark?

I have been playing the "roguelike" video game Dead Cells a lot recently, and I'm intrigued. Can I create a roguelike megadungeon by procedurally generating dungeon levels semi-randomly during play?

What frameworks can I put in place for managing denizens, factions, and the dungeon ecosystem? And the town economy??

Can I make structures to keep up pressure on the players to keep moving, think on their feet, manage their resources and just get out alive - and keep it fun? 

Should I play the Master of Ceremonies (thank you Apocalypse World) or the traditional the Dungeon Master, Keeper, Game Master, Referee?

Am I actually good enough at building dungeons to be able to build a mega-one??

If you have any suggestions, or helpful links/resources, please let me know in the comments!