I will preface this with an apology; this is a ridiculously long reply, and I'm sorry for that.
You have to remember that our words get used against us a lot. When you have millions of people read something you say - it's super easy for it to get picked apart.
Definitely. It's pretty annoying to watch players do that, especially when there's clearly good intent behind the message.
That being said, the flip side is that there will always be a vocal minority trying to tear everything that is ever said by a Rioter apart. Nothing will really change that, but lowering the amount of transparency can have the opposite effect of what might be intended. An uninformed playerbase is more likely to try to pick out faults, since they are potentially unaware of why certain decisions may or may not happen and just assume outcomes.
A great example would be the people that complain about Riot being greedy. Is Riot greedy? Of course not, but they have to make money. With clear policies and information around eCommerce, it is likely that sort of complaint would be considered baseless or ridiculous by the vast majority of the community rather than people getting sucked into the negativity spiral of that vocal minority.
I personally like the over-communication, (and subsequently frequently make mistakes) approach but that just means you guys will have to give me some flexibility to say stupid stuff and not hold it against me too much.
Honestly, as long as communication isn't perceived as out of touch by the community, things tend to go pretty smoothly. Rioters make mistakes all the time, but it's when those mistakes make the community feel as though the response is canned or not actually addressing anything that people get frustrated.
I'd rather speak frequently and casually and have be given a hard time sometimes than force everything I say through a strict filter to think about all the ways it can be taken wrong
I'm not sure if you have to choose between those two options, necessarily. Many of us, especially the ones that are truly passionate about the Boards, understand that software development is all about change. Hell, I've experienced this myself (albeit with a much smaller community, around a thousand people). Really well-crafted responses from people in perceived positions of power, even if they don't necessarily match the opinions of the playerbase, tend to be very well received.
Krylhos' response in this thread is a fantastic example. The thread itself has a lot of people that are very passionate and very frustrated, but his response was perfect for the situation. He expertly tackled the concerns that were raised in the thread and simultaneously explained why things might feel strange and what Riot plans to do in the future. This response was fantastic, despite the fact people still disagreed with the premise and the fact Riot is working on the Boards rather than the vBulletin forums.
TL;DR: It sucks that people read way too far into comments. For those of us that are reasonable, it's really frustrating that this distinct minority is able to influence interaction so much, and a lot of us really do understand that Rioters are human and that mistakes are just part of daily interaction.
I would love to see what might happen if, at least for a little while, you guys working on the boards could trust us not to tear you apart. I know it's hard, and we as a community have a lot of work to do to make that possible. We have this tendency to beat on Riot for what hasn't happened rather than commend you for what awesomeness has happened or what's being worked on right in front of us, and that shit is not OK.