1- Wait for the 8300
2- No wifi on 8800
3- personal decision
4- I am betting that RIM won't abandon the trackwheel completely. One of the RIM insiders will have better insight into that. i like the trackwheel too.
5- I am not upgrading yet, because I can't see anything yet on a 8800 that just floors me. I'm not going to be watching any stinking videos on a BB, I don't need the music or the extra media card.
So... you are sorta like me. I would like the GPS probably would LOVE to have that. But I have in my car... so. I am keeping my 8700g, trusty and reliable for now. In six months... ?