'Have both the Bat and the Shark ('05 SEEG / '09 SERG) I know the frames are different, but I've had both bikes to the 4 Corners and all points in between.
The Bat is much more nimble at lower speeds, parking lots, Eastern Twisties. The low speed turn-in is effortless. You don't see too many Sharks at Motormen Competitions... Hi-Speed Stability is fine, never had any kind of "bagger wobble" at any speeds conditions, even in sweepers at 90 with no hands. The aero is fine, (10" standard type windshield) wind hits my forehead (6'4") the bike pulls past 120 without running into a wall of air ~stock 103, it did (run into a wall at 110) with a taller windshield that I had on the bike for awhile. The '05 came with the dog dish and vented lowers.
The Shark really shines on top. It can be turned aggressively at lower speeds (Eastern Twisties), just requires more effort, it is more ponderous in the parking lot. The Hi-Speed Stability / aero of the Shark is without equal in the Harley world (once we installed the 12" WindSplitter, Flaps, GADS Lower Triple Tree Deflector, Vented Lowers and '10 & later Brackets ~ it was a buffeting nightmare in stock trim). Nothing but clean air at any speed, no buffeting, with or without a helmet, the only bike I have ever ridden that I can smoke a cig comfortably on the Interstate. 'Have not run into a wall of air yet (at 4k+ rpm), maybe the 117 has something to do with that

The Shark is easier in cross winds, to me, the faster you go, the more stable it is, cross winds at lower speeds they are about the same.
Both bikes have Chopped Tour Paks.
The aero on either bike doesn't change with "The Ball & Chain" aboard, and she is fine with either (once we got the Shark figured out).
Rain protection is about the same for me on both, my knees / upper shins are the first to get wet (34" inseam).
JMHO, your results may vary...
It's good to have choices...
On the trailer thing, if logistics / time doesn't make sense, than trailer (or fly and ride for that matter) is the way to go... Last year we ran across 3 couples on the West Coast, from Oregon down to NorCal, we were leapfrogging and finally got to meet them at a scenic pull over, they were from PA, (2 owned Harley Dealerships) and have been taking motorcycle vacations together for years, and fly & ride is the way they go, because of limited vacation time ~ it made perfect sense to us!
Sometimes life just gets in the way...
The thing about trailering 2 baggers from Jax to Daytona is still got me scratching my head

especially when the ride from Ponte Vedra to Daytona on A1A is one of my top 5 rides in Florida.