I found
Sid Meier's Pirates! in a Best Buy bargain bin on Friday night and snapped it up. I've been playing it pretty much nonstop that evening and all of yesterday. About 1 AM this morning I finally achieved the rank of Governor:
I also went through the game resource files to see the images of the other post-pirating professions.
It's quite a fun game--I love the sea combat and swordfighting. Dancing wasn't that hard, as the moves are organized into pattern clusters, and I'm extremely good at pattern recognition. I didn't do very much land-based combat or sneaking into towns, though.
I played through
Pirates! on Apprentice level (the easiest difficulty) in the 1660 era, and I still felt it was challenging, but not so much so it impeded the fun.