(1) The ObjC/GCC thing happened in the '80s, and didn't prevent them from doing things like shipping (and updating) plenty of GPLv2 software with OS X when it first came out in the late '90s/early 2000s. Additionally, WebKit came out in 2005, and was forked from KHTML, which was LGPL. They didn't have to choose KHTML, they could've written something from scratch or used something else. Their issue is obviously with GPLv3, not the GPL in general.
(2) Many, many, many people, including many people in what you would consider the hacker community, have serious issues with GPLv3. One might even say that for those people, GPLv3 is "doing nothing but making it more inconvenient for its customers to get modern software." And it's not like GPL < v3 was a universally beloved and accepted license either, it's pretty much been a font of endless flamewars since its inception decades ago. I personally think it's a great license as long as developers and users understand its requirements, but let's not kid ourselves that it's something everyone should universally embrace and use regardless of their own goals and ideals, or without fully understanding what requirements it imposes.
(3) Back in the '80s, Jobs asked RMS if the ObjC front end could be distributed separately and linked by the user, and therefore not fall under the linkage requirement of the GPL. RMS said he'd ask his lawyers. He did, and his lawyers said it was a gray area that could potentially be abused. RMS decided to tell Jobs that he would not be OK with that arrangement. Jobs said "OK", et voila. GPL'd ObjC front end. That sounds more like grownups resolving a disagreement than pwnage, but whatever.