How long is the trailer? If the length is longer than the width it will want to track straight, but short and wide can get you into a fish-tail pretty quick. Are the wheels closer to the rear of the trailer, or centered? Where is the load placement? near the tongue, center, or rear? All of those variables factor into play...
No problem, I tow wide load office trailers for a living and the 8 wides are not any wider than the mirrors on my F350. Much easier than you think. I also pull 12 wides almost daily and have done a couple of 16 wides what im getting at is it's MUCH harder than you think to wack someone with the side of the trailer. Go for it!
It's 40 degrees and we had snow yesterday. How much of that do you ride in?
I don't think it's a big deal trailering to Daytona in February. IMO the mistake is going to Daytona period.
I rode across the I-25 Raton Pass at the Colorado/ New Mexico State line in April 2004 in 6" of fresh stuff, at over 12,000'. I didn't even take a long sleeve shirt- wore just my leather jacket with liner, a tee shirt, blue jeans and rain gear/ gloves. Coloradoans think most all Texans are crazy and my plates tipped me off to them. Never forget the looks I got.
So to answer your question, I don't ride in that stuff much. I don't seek it out but I don't shy away from it. And I learned a lesson, be prepared and take proper gear for ANY weather event.
I live in the heat for a reason, I'd hate living in a cold climate. Ever ride in 100+ temps for 5 months out of the year? I do every year. But I'd never trailer to a rally or any destination for that matter. Just goes against everything I stand for. Paying the Weather Gods their pound(s) of flesh makes the good riding that much sweeter.
While we're on the topic of weather, anyone go to the Harley 100th in Milwaukee back in '03? It was a monsoon for 900 miles on my way home, didn't let up until I got to Little Rock. Nothing like hydroplaning at 75 mph to have you living in the moment.
'03 Deuce: 88k miles and counting, '11 RGU: 70k miles and counting.