With your lenses, I'd have the 16-85 on the camera most of the time, but the 100 macro, 300 and TC will come into their own often enough to make them worth the bother. You can stitch a panorama, but you can't always crop enough to replace a good telephoto. Adding the DA15 for starbursts at night is a trivial extra load.
I took a crop kit to Italy last June, and got best mileage from my DA15, DA21, FA31 and DA55-300. The 10-17 fisheye was a boon on rare occasions, and the FA43, DA*55 and FA77 were rarely used, but still produced some of the best images of the trip. Pix
HERE if you're interested.
---------- Post added 16-02-18 at 11:44 AM ----------
Originally posted by normhead I can't believe how people constantly underrate this lens as a landscape lens. It may not be the best wildlife lens, but it's the best top quality landscape lens that can also be used for wildlife.
I'm still considering buying the DA*60-250 for my Antarctic trip, even though I will be taking the K-1. Like the OP though, I don't think I would have the heart to leave the DA*300 behind, and the DFA100WR with the TC can fill some of the gaps.