1. John Davison is a really really smart guy, way ahead of the curve. He was behind all of the freaking amazing shit that 1up/EGM was doing back in the 2006-2008 era. He also was behind making GamePro not a shitty magazine too. Albeit, both of those properties went to shit, but that happened after he left.
2. GiantBomb holds the hammer here. Whats really valuable is THEM. Their personalities. If things go bad, they could cut ties and start again. They've done it before, they can do it again. It would be a similar situation to when Bungie left MS. Bungie didn't like being under MS anymore and said "We're leaving one way or another", and all MS had to decide was whether or not they wanted to keep the Bungie brand name.
I like Davidson, but Davidson has left three organizations now in what, five years? And each one was a big media company that subsequently crumbled.
When you get big, your publishers demand more revenue. It's a Faustian bargain and I can't think of many examples where it turns out for the better.
For some game developers, for example, I can see how it gets better with more access and more revenue. But for a small site like Giant Bomb with a handfull of people doing a weekly podcast and videos, why do I want or need them to take that risk? For what? For virtual studios? For "up to the minute" reporting? No thanks. Nobody cares. That's not why we like the site.
As for your second point, again, haven't we seen big media companies buying brands for their name recognition and then gutting them afterwards enough times to know that it is an established pattern? Heck, it's a pattern of business in general. There is a reason employees get nervous when mergers happen.
Perhaps you are correct that the personalities here would just "start over" again, but I'm certainly not throwing money to them next time. I've lost faith that they are trying to be good stewards of a small but good thing. Instead they stupidly care about "get bigger!"