>2. If the answer to #1 is yes, how does Apple avoid this problem? Are they also licensing from Microsoft? Or is Apple in some sort of a mutual cross-licensing agreement here to fight the common enemy Google?
They are all in a sort of standoff, as they cannot sue each other without putting themselves at risk of counter-claims. In addition, there are a number of cross-licensing deals between various large patent-owning entities, as you correctly surmised. Microsoft found a way around these issues, by suing Android implementers (such as Samsung, HTC, etc.), who do not have such large patent portfolios with which to make a "second strike".
A good question, which probably is the reason why Google didn't drop Motorola case against MS (even though it wasn't a good one). But really Google can do more than that.
I wonder if (and how far) Steve Jobs was looking into the future when he did this, and how well, if at all, it has served Apple considering their more impressive innovations since then.
I would think Steve clearly saw the onslaught coming up and probably had an early director part as well - By end 90s MS had become a benefactor to Apple and both were no longer threats to each other. The enemy now was Google and its plans of global domination - I suspect, Steve - the master mind that he was saw the merits in ganging together against a common enemy.
It was common knowledge from early days that Android infringed on several OS and mobile patents. Also note Andy Rubin sold Android predecessor - Danger OS to MS along with all IP. It was just a question of when and how the IP assertion happens.
They are all in a sort of standoff, as they cannot sue each other without putting themselves at risk of counter-claims. In addition, there are a number of cross-licensing deals between various large patent-owning entities, as you correctly surmised. Microsoft found a way around these issues, by suing Android implementers (such as Samsung, HTC, etc.), who do not have such large patent portfolios with which to make a "second strike".