I feel I should wrap up my thread by describing my findings as a practicing MCU noob.
First of all, I did start with a PIC and a PicKit1 proto-board, but I never had much success with this. In all fairness, the PicKit1 is reasonably old (although USB based) and so had all kinds of trouble getting software to work, not made easier by the fact that I'm a Linux guy. A newbie with the PicKit2/3 on Windows might very well form a very different opinion.
Then I got a hold of the official Atmel avrisp mkii programmer with various ATtiny's and quickly wired up a programming board and installed the software with an apt-get onliner command. Within a few hours, I was writing C samples, compiling to hex, transferring to MCU and running the program on a breadboard. Amazing, as a software guy used to high-level abstractions and abundant hardware resources, to see the other end of the scale with an IC the size of a the head of a match, consuming just 7uA when sleeping.
So anyway, it may not apply to everyone, but for those used to standard open source tool-chains without a need of an IDE, I have to say the AVR experience with the tiny is very KISS and a hell of lot of fun. If/when I feel the need to move on to more advanced chips, the path seems paved and clear.