I would just like to answer on one aspect of your question particularly.
If you are adding personality, make sure you don't get lost in something localized. What I mean is, you are adding flavor by the whole personality thing, by say adding a line - "Let's grab a beer, some fries and watch some football."
That line might be something that would be pro-region. That would definitely not fetch you personality points where I come from.
When my chrome tab crashes, it says "He's dead Jim" by quoting Leonard McCoy. Most people I know don't even know where the quote comes from and who Leonard McCoy is! They just like that instead of a ERROR it shows a sad smiley.
Sad smiley is something universal - try adding personality with something that won't get localized like the he's dead jim or grab a beer or something that might not relate with the whole of your audience.
This is only very vaguely related to your question, but I should point this out since we are talking of personalities.
In this question, What are the best practices on religious holidays?, people have constantly suggested that it might offend certain users if you touch on the wrong greeting method for saying happy holidays!!
Similarly, if you are adding personality by adding say halloween related stuff, it might not go well with people on the other side of the world who are not aware of what halloween stands for!