Q: To upgrade or not?

Well, speaking as a person who has never seen anything on iTunes that makes me want to upgrade past version 7.5...

Really. Look at how you use iTunes and what you need/want.  Most improvements post version 7 have been directly with marketing or a few things indirectly dealing with marketing such as Genius which requires you have an account which I do not want and sends your music use data to Apple.

I have no technical data but iTunes is, IMHO, becoming bloatware with trying to do too many things at once, and the more intricate it becomes the easier it is for it to hog resources and for problems to appear.  Again IMHO they should have kept iTunes as a media player and split off other things such as syncing and selling stuff as related but separate applications.

The nice thing about 7.5 is I honestly have zero problems with it.

Since you have no i-gadgets that eliminates the need for a higher version on that front.

I guess at some stage you will eventually need to upgrade, but I am putting that day off for as long as I can.

If you really want to do 10.6 I would wait a week or two until the dust settles and we can see how many persistent issues people have.  Right now we're seeing the usual flurry of issues that may just be bad installs on systems which may already have issues which you probably would not encounter.  I let others find the problems first.

One quick doublecheck Klaus ... are you using the Store for music purchases at all?

Downloading past purchases from the App Store, iBookstore, and iTunes Store - http://support.apple.com/kb/ht2519 - enabled with iTunes 10.3 and newer; not available in all countries; apps, books (not audiobooks), music, t.v. shows, and movies. Movies available in the USA only. Downloading previously purchased movies and TV shows requires iTunes 10.6 or later.  Discontinued items not available.

good-O. I'd keep an eye on your security updates, then.

A good rule of thumb is that any webkit vulnerability is an iTunes vulnerability. With any luck, most of those will be being closed by the general OS security updates. However, there's a few vulnerabilities that get noted that are specific to iTunes (rather than webkit) that might create an iTunes Store issue.

So I'd just keep a weather eye on the Security Updates articles for iTunes, just to make sure that there's no holes appearing there in the 9.2.1 version that you're unhappy with:

Apple security updates

I had so much trouble with 10.6 that I went back to 10.5 and had to do some more troubleshooting.  Finally, I got my IPOD touch cleared, reset, and synching to my computer again. I got advice on settings, uninstalling, error messages, and many more tips to finally get my IPOD running.  I'm so grateful for this community and those of you who take the time to document step-by-steps and things that work for you. Thanks to all in the community.