Fun loop. I've done it in every season and every which way from all 3 THs(used to be able to park overnight at Lake Chinnabee) as a dayhike, nighthike, and quickie overnighter. Still do it a couple times per year, because I always enjoy it.
Need to do some hiking to make a hiking video, though!
Merino doesn't fare well with our humidity(socks only for me), and hiking in a shell here is likewise a no-go, as the B in WPB is mostly wishful thinking.
Combining the two, your clothing has about zero chance of transporting moisure away, so you get wet and stay that way.
While "testing" merino on a short hike here in AL, I wet out a 150wt top under an OR Ferrosi jacket that's much more breathable than a shell in ~3 miles of uphill at 32F.
"Dry is warm", as the saying goes.
btw, if you want to split up the Skyway/South Cheaha Loop, I particularly like parking at Turnipseed Hunter's Camp when the temps are lower, hiking up to the Pinhoti, down that to Adam's Gap, then taking Skyway to the first creek crossing, where there's a good campsite.
If it's warmer, I'll press on to camp on the Chinnabee above Devil's Den. Skyway is the worst for bugs in warm weather, IMO.
Couldn't find a pic to show you the site, but it's a pretty nice one, with several level spots to choose from, and a nice sized fire ring with places to sit around it.