I've seen a couple of different jersey concepts for the Flowers, so I'm not exactly sure which one you're referring to, but I haven't seen one I didn't like yet. As for the team, we haven't been very good the past few seasons, so the fanbase has become a really encouraging one that doesn't care much about winning (which, as a Boston sports fan, is frankly refreshing). There's sort of a mentality that we'll be able to turn things around next year if we hit a blessing or two, though.
As for voting, there's not a huge amount of strategy, at least that I know of - I'm by no means a blaseball expert. I've accumulated dozens of votes but I'm holding off on using them for the moment partly for that reason (and partly because I don't want to vote for fourth strike or home field advantage if the Flowers don't end up in the bottom four). At the end of the day, though, I see two options: you can either vote for the things that will help your team, or you can just vote for whatever sounds cool. Again, there really isn't a wrong way of doing it.