I've had 4 campers, two 12' box pop ups (~15.5' tow length), a 22.5' tow length travel trailer, and now a 29' tow length travel trailer.
The pop ups and smaller travel trailer were all roughly the same when opened up around 22.5' - 24'. I could camp in pretty much any spot that allowed the trailer height, and towing was a breeze.
The larger 29' trailer can't fit into most spots due to it's size which is a real pain. I've been VERY lucky to find open spots that would fit it after finding several times the spots that were suppose to fit, could NOT and the campground was booked up. Luckily cancellations allowed me to get spots that fit.
Towing in wind or storms can push the rig around, not sway, but as one single rig from the wind sail sides on a larger travel trailer. Stiffer side wall LT tires, heavier truck, and stiffer anti sway hitch system all help. My new truck is lighter and it only has P series tires so it's not to bad but not great. Blue Ox Anti sway hitch helps pretty good when enough tension is put on the bars.
BUT with 40 - 45 mph side winds, it still can get dicey. In that case just slow down even if it's slowing down to only 50 mph as the rig should handle better.
I wouldn't fret over only a couple of feet in length, but 5' or 6' in length could make a difference in towing ease and fitting into a nicer, shorter camp site.
That said, I prefer bunks when the kids will be using it a lot.