I really struggle with this question.
I have a nice trailer (Hannigan Sierra) that pulls great, looks good and doesn't bounce. I bought it last spring and have towed it on 4 or 5 trips including Americade and Wing Ding, and a few other trips that crossed several state lines.
It is convenient to have along because of all the stuff it holds and you can take all your riding gear off and stow it easily, carry a cooler , etc etc.
But.......when it is loaded, it is a load.
I see guys post all the time ....."I don't even know it is back there" and all I can say to that is.......pure BS! I feel it EVERY time I slow down quickly or stop. Coming back from wing ding, I was rolling through West Virginia on a misty morning with wet roads in the up and down twisties and I had to run a LOT slower knowing the trailer was there .....especially in those down hill switchbacks on a wet road. Even when I am rolling down the slab at 75 or 80, I am always aware of not getting into a tight situation due to the additional distance I need to stop......or scrub off speed quickly for any reason. Pulling a loaded trailer safely requires a completely different concentration level and riding style than riding without. Sometimes it is worth the hassle, sometimes it is not.
A couple of weeks ago I went to Morphs Wiki ride in WV for 4 days and only took the Packit Rack for my Wife and I and had a much better time on the way there and back.
So for me it is a toss up......If I am going somewhere to stay for a few days and "day ride" I will pull it and leave it at the hotel until the return trip but if I am traveling and will be a different place each night, and have to pull it continuously, I may leave it. For me, packing lighter and leaving the cooler is a fair price to pay for having a lot more nimble vehicle and a much more enjoyable ride. :thumbup: