[wstrange]

Realistically, how many people would have paid for something like Google Reader after getting it for free for so many years? I think it would be a tough sell and you would have witnessed a lot of complaining...

On the other hand, the negative PR they have gotten from Reader (it's pretty much the poster child for the "Google cancels products" meme) - they probably should have kept it around, even if it was not strategic.

[acdha]

I'm pretty sure anyone working at Google knows how to put ads on a free service but in any case, I saw a lot of people calling for a paid option in the period between the de-featuring for the botched Google+ roll-out and actually closing the service down. That would have been a natural approach: free version has ads with some sort of “Pro” option to remove them.