Hi, I had almost no sailing experience when I bought my H-16 and am completely self-taught. I use to think the Hobie 16 could be sailed solo and my limited experience was the reason for all of my troubles. Experience has changed my opinion. I have had my boat 2 years and these are my experiences related to going it alone on this boat. I weigh 140lbs and am 5'7" Raising the mast is extremely difficult for me, especially when securing the cable which keeps the mast up. Sailing in light to medium wind is fun, unless a stronger wind appears when this boat becomes terrifying for me. It is just too fast for me to control safely in 15-20 mph of wind. Righting after a capsize is impossible for me. I have the Hawaiian righting system and I am not skilled enough to right this boat solo in heavy wind.
I am sure more advanced sailors will disagree with my comments concerning rigging and sailing solo. A more skilled sailor might do fine solo. As this post is negative I feel I should mention. I sail my H-16 almost every weekend, with someone/anyone, and sailing remains enjoyable for me. I love this boat it's fun and enjoyable when I have a crew. But without a crew member I leave this boat in the driveway. I also have no problem finding crew. Once people learn you have a sailboat they will find you.