Back in da day, when I was teaching in Sydney, I would regularly ride solo as I had the time during the day whilst everyone else was at work. Also in big winds I tended to ride solo (+30 knots) as there were only a few of us game to go out when it got a little over the top, especially at Cronulla when it was BIG in a screaming S'Westerly.
I reckon solo kiting rules if your competent in your ability to handle it. It's always best on your own IMHO. If you have rarely kited alone and aren't sure of your ability to get yourself out of trouble if the need arises, then dont do it. Never underestimate the conditions or overestimate your ability and you will always be fine.