Do you need the same sidebar in all pages? wordpress gives you the ability to make other templates.
I did add custom sidebars and quickly found out that not all widgets can be used on more than one sidebar which frustrated me! FWIW and as an aside… Widgets make so much more sense to me than hand coding php, but that is just me! I am not a programmer, I train horses and teach riding and generally work long hours. :)
So, I wanted to stick with widgets, have more dynamic content in the sidebar so that it changes as you suggested. Finally I found the solution… TS Custom Widgets (Tom Slayer). So now I have 1 widgeted sidebar.php and a nice and easy point and click way to manage which widgets and content appears beside any page or post on my site. Really cool and worth a look if you need this functionality but don’t want to mess with code.
A few other changes have been made.
A few more in the plans, first off a wider content area as suggested, thank you!