Bob,
For me, the 55-300 has been such a great lens that the only reason I'd consider getting rid of it is if I really needed something faster. Since I do most of my shooting outside, the speed isn't that big of a deal for me at this point. I don't use it too often at the 300 end, either, but it's nice to know that it's there when I need it. One thing to consider to is the weight of the lens--the 55-300 is a lot lighter in weight than any 70-200/2.8, which will make it a lot easier to carry around.
As for my 17-70, again, the main reason I'd want to get rid of it is if I really needed something faster. A second reason to get rid of it would be if Pentax ever came out with the DA17-70 in a WR version. Like yours, mine spends a lot of time on the camera. I did have the 16-45 for a while and I really did like it, but it just wasn't quite long enough for me. Between using both the 17-70 and the 16-45, I really don't think that losing 1mm on the wide end has made much of a difference at all--if I need to go wider, I can usually just back up a little.
If you're really wanting to get into WA photography, you might want to consider keeping the 17-70 and saving up for a "real" WA lens like the Sigma 10-20 or DA12-24.
As for macro lenses, I would most definitely recommend the DFA100--great IQ in a nice lightweight package.
HTH,
Heather