It can be. A shorter one will react quicker than a long one. You just need to factor that into the equation.
I never got used to 28' trailers or those 20' intermodal trailers. Could put a 48' or 53' trailer in some of the tightest spots with little effort.
It's not about the length of the trailer. It's about the distance from the hitch point to the trailer axles. Smaller the length, the more sensitive the trailer is to steering input. Longer the length, the less sensitive. Neither is necessarily more or less "difficult". It helps to have the distance as close as possible sometimes, so you can control the trailer easier, and maneuver in tighter spots. You just have to be more on your toes, because the trailer reacts faster. In my opinion, that is a blessing.
I don’t know but I find more difficulty backing up bobtail than backing a 53. Lol, I seldom disconnect from my trailer but when I do, total confusion kicks in.
I back my truck and trailer through an S-curve and a 10' wide gate onto the street. No problem. Come home after a couple weeks, and I can barely back my pickup through the gate without ripping the mirrors off.
The school I went to had a 28' pup for yard practice. The school was SERIOUSLY "fly-by-night", so when they told us, "If you learn to back a pup, you can back anything!", I thought it was just more of their BS. When I went to orientation for CRST, it was my first time angle backing a 53'er, and I got it in the hole in one shot, like it got sucked in there. I actually got a standing ovation, but only because there were no chairs. I worked at CRST from June 1 to July 10 of 1995, then found tanker work and never looked back.