Going from memory riding solo and driving an outfit you need a totally different outlook and handling technique but I quite enjoyed it. I have fond memories of poodling along with my left elbow resting on the top of the sidecar.
My only experience was with the Canterbury Double Adult, and it was a very big sidecar but I don't ever remember my Golden Flash struggling with it and here in the south west it's very, very hilly. I would imagine a light single seater would be a doddle. The Canterbury had windows front and back with three on the sides and one seat behind the other. It had a canvass press studded top which could be rolled up and secured with straps, so a nice sun roof and you could easily chat with your passenger. I do remember on more than one occasion having to retrace my journey to look for the perspex windows that blew out . . . so I must have been able to go r-e-a-l-l-y fast!
There were other benefits that I remember, and not being a car driver in those days, that I liked, such never having to pull my bike onto the main stand - just leave it in gear. Get on it like you would a horse, easy position to kick start it, somewhere to keep your waterproofs and anything else you want to carry.
My best friend was a motorcycle salesman for Kings of Oxford and he got it for me for a knock down price and helped me fit it to my GF. The one thing we forgot was to firm up the steering with the damper and on my first test ride, being used to riding solo, I opened the throttle and nearly hit the wall. I remember you had to fit it with a certain amount of lean out and tow in for stability.