Install TurboPrint as the inbuilt printer support is rubbish and the bundled Graphics Publisher program is one of my favourites and in conjunction with Photogenics allows my to print high quality images. As for upgrading OS3.9 beyond BB1+2 generally I view it as fun little voyage of discovery i.e. upgrading WHDLoad as new ports fail to work, setting up AHI when games like Heart of the Alien don't have Paula support without it etc!
It's all part of the Amiga charm keeping all the dependencies chugging along! Heck it's always been thus; I remember having to run the Napalm Game's setup program prior to using Key to Driving Theory to get it to run correctly from the CD = crazy hacks all round!