The Daysailer weighs 575lbs if I am not mistaken (not including cargo). The trailer should be around 500-600lbs. You are probably looking at towing 1200lbs.
I have a Toyota Tundra, so I can not tell the difference between when I am towing the boat and not, but I imagine most vehicles could pull this load. The thing that I would watch out for is the type of tire you have on the towing vehicle? Boat ramps can be slippery.
Outside of that, I just bought my Daysailer a year ago. It is my first boat, and I am always learning. However, it is pretty forgiving boat. Where I live at, we typically see winds around 13-15mph on average, with gusts to 20mph (sometimes 20+mph). I have been watching the wind reports for a minute now
None the less, the boat has a tendency to sail upwind on its own if you get overpowered, which will stall you out (good thing). I have had my boat heeled over on it's side with the rail dunked in the water, and once healed over enough, it will start shifting upwind on it's own to level back out (vs go over). I believe this is because the rudder stops making contact with the water, and the wind will slowly rotate the boat on the centerboard, shifting it to head upwind. I believe the term for this is "self righting".
Down wind is another story. There is not really an auto correct feature. I just make sure that I do not sail directly down wind, I usually keep some angle.
Like I said, I am relatively new to sailing, but my boat seems very stable. It is fun and easy to sail. +1 for the Daysailer