Brief backround - I have enough expeirence that I'd sail a sunfish in just about any wind. I got my first "real" sailboat last fall - my DS II. I participated in a few learn to sail days my local sailing club offers on one of their Flying Scots - they were helpful to get experience with knowledgable assistance. Most sailing I did on those days was close reach or beam reach - no running. I have had my DS II out twice, first with no wind and again this weekend finally in good wind to learn (less than 10 MPH) with my wife as crew since my mother in law was available to watch our 5 year old and 1 year old. I will take the kids out in the DS II when I'm much more confident in my abilities and most likely not until the 1 year old gets a few years older (I'd probably take the 5 year old now, but not as my crew). My sailing is therefore limited to when someone can watch the kids. This past weekend I felt quite good and confident in being able to handle the boat and wondered if I'd be able to sail it single handed in reasonable wind. The lake is a smallish western PA lake with shifty wind at times and occasional puffs, but nothing unmanagable. Shore is closeby and I have auxilary power if I needed to drop the sail.
My question is whether it's foolish to even try to sail single handed yet? I see 3 or 4 opportunities to get out myself in the near future if it's feasible, but probably once at most if I decide I need a crew.
For those more experienced in single handing the DS II, when did you start?