Now that I've abandoned the Known World map as a home for Zent-Mer, I have the happy task of creating a new wilderness map. I'm weighing how much I want to plan out now, and how much I want to leave to random chance and/or development during play.
On the one hand, planning in advance lets me do an awful lot of "stocking" ahead of time. Starting play with a fully-detailed wilderness area is certainly an attractive proposition.
On the other, it's a lot of work up front. It's possible that a more organic approach, like generating "unlocated" hex contents and assigning them as the party travels, could be a good compromise. Maybe with a few large hand-placed landmarks (like oceans, the big mountain ranges and forests, etc.).
I'm also trolling around trying to round up as many random terrain / hex contents / inhabitation generation methods as I can, in order to compare them and arrive at a solution for my campaign. So far, the 1e DMG, Kellri's (completely indispensable) CDD#4 Old School Encounters Reference, the JG Wilderlands of High Fantasy and Dave Arneson's First Fantasy Campaign are the main sources. (If you know of any others, hook it up!) I also have a copy of the 2e-era "Worldbuilder's Guidebook", which takes a slightly more "top-down" approach than I had initially planned, but still could be worth another look. (One of the better supplements from this era, for my money.)
Once I come up with an overall system I like, the real fun of actually generating this sucker comes in. Me and the Ravaged Ruins tables are gonna get very cozy for a few minutes.