MediaMonkey rocks, IMHO.

I'm going to blasphem and say something like Visual Basic 6... Or any very high level language.

That's because for me, learning first about higher level stuff, being able to focus more on what I want the program to do, and not the nitty gritty of memory management (to mention just one difficult area), allows me to learn at my own pace.

I first learned QuickBasic, then Turbo Pascal, then Assembler, then a little C++. It was easy for me to understand ASM (even machine code) after Basic and Pascal, plus it helped me understand how those worked.

It could be the other way around I guess, but that's what worked best for me.

Portfolio supports everything under the sun (well, not quite), has advanced handling of metadata, searches are very, very fast. It's designed for professionals that work with thousands of images. You really have to explore the program to see everything it can do.

MrCrispy, you may want to take a look at the "Master Keyword List" window to do what you want. You can also use Smart Galleries to do the filtering, albeit it's not as quick as you want it.