I'm in the small trailer category. Lots of back roads, high elevations, twisting one lane, blind corner, cliff on one side, dirt road, boondocks and back country national forest campground - kind of pulling. But for all that the tightest area and requires the short trailer are the actual national forest campgrounds, with skinny curving roads with wood curbs on both sides, boulders and trees right next to the roads, and short driveways. 21' foot trailer was doable in the campground, barely, but the 8' width was scary on the one lane forest service roads next to the cliff while going around corners. I ended up with and am very comfortable with a 17' 7.5' wide trailer. Just the two of us, with a slide, and full queen. The problems are crawling over each other in and out of bed; not much room to toss things and leave them for a few days.
Of course I tow with a 3/4 ton crew cab long bed, whose overall length is longer than the overall length of the trailer. Sometimes I put our Polaris RZR in the bed of the truck.