I told myself I wasn't going to get caught up in the CSM endorsement deal. But here we are; I'm writing this post and you're reading it, so I guess we better get on with it. :)
My ballot will include; Sugar Kyle, corbexx, Mike Azariah, and Jayne Fillion, not necessarily in that order. I'll do more reading and may flesh it out more, but my ballet may stop with those 4 names.
I look at big pictures. I'm looking for candidates that represent the under-represented areas of the game, even if those areas aren't places that I spend a lot of time. Sugar is lowsec, corbexx is WHs, Mike is missions, and Jayne is NPSI roams. Meanwhile, I assume that the null blocks will do their thing and get their candidates in - the candidates above fill out the council and provide some counterbalance. That's not my entire criteria, but it's where I start.
I don't know corbexx, Mike, or Jayne except by reputation and what I read on the internet. I don't listen to podcasts. I do read Mike's blog. I read the minutes, and forum posts. And I'd like to meet some of these guys if I can make it to EVE Vegas this fall, assuming they're there too.
Sugar will be my #1 vote on both my accounts. I'm not the only blogger to say that (see here and here and here), and I'll try not to repeat what others are saying (even though I agree with them). Sugar's the exception to my roster because she's the one candidate that says hello to me when I login. She's listened to me ramble on more than one occasion with patience and good grace. To be clear, I'm an old highsec carebear and not her target audience. But I've always felt welcome and not a "lesser" player because of the career path that I take on. And months after a random chat with her, I see things I said showing up in her meeting prep notes or my questions being asked in the meeting minutes. Everyone says she's a hard worker (and I think that's true). But there's more to it: She's organized. She pays attention. And she listens.
Don't overthink your vote. Don't assume that Sugar is a "lock" and put her lower on your list. If she's truly your #1 or #2, then make her #1 or #2.
The magic of transferable ballot math will take care of the rest.