Thanks for all the input guys!
Pretty much narrowed it down to a 330i sport / zhp or 530i. Still wrapping my head around the sport package with the e39, but it looks desirable as well.
Again, won't be seriously looking for another month at least, but it have a fairly good idea of what I'm going after. Will definitely have to take a look at a few and get a feel
As for space... The e46 hasn't been BAD....but there are times when we use the gf's accord because it has so much more room. Makes me crave the 5er. For snowboarding or other big stuff, I have a Thule roof box and racks that will fit either car in question.
Windwagen, thanks for the offer I may indeed meet up over the summer and take a look! I feel like I haven't paid enough attention to e39s at meets and such.