It has been a very long time since I did any random dungeon creation. Back in the day it was supposedly an easy way out to run an adventure. Not much planning, a few rolls and presto you have an evening of entertainment.
I should have know better. I was doomed from the start.
To start with, I couldn't really use completely random tables. This was to be insert in an already designed area so the start and ends had to come together, and the inhabitants had to fit in a subset of what was likely to be found in these underground caverns. So I had to build my own random tables. I supposed whether you use somebody else's tables or your own, somebody has to build them.
To make a long story short, I could have drawn and populated a set of natural caverns far more quickly that generating random caverns, making them connect and populating them with tables. Perhaps there was a change up from the players view; if I had populated them not so randomly my stamp may have been on that and the characters might have been less surprised. However, I don't think so. Personally I think I stay ahead of the characters and am still able to surprise them no matter what patterns of my behavior they believe they have deciphered.
I found that I was not crisp with the information on this random map creation. I made mistakes, had a little trouble orienting the group in my descriptions and lost my place here and there. Making it in advance, whole cloth from my own imagination, somehow makes it stick better in my mind. Plus I have a little time to review before the adventure so I am much sharper with details.
Now, it really didn't turn out all that bad. I was disappointed in my running of the last outing; it felt a little bit awkward and slow but we got through. I just have to face facts, after thirty years of game mastering I am just more comfortable assembling my own adventures manually, with some die rolls of support, than to just trust it all to chance. I am not afraid to try new ways of running games, or game content and will continue to do so. This does just reinforce that you should play to your strengths.
I have said it before and I'll say it again: the dice never lie. I suppose the real wisdom is knowing when to ask them to speak.