Re: Good starting boat with some speed, but forgiving while learning as well?
Keel or centerboard?
Trailerable or beach boat?
Monohull or cat/trimaran?
The list of boats fitting your desires is endless. There are lots of small centerboard or keelboats that are relatively easy to learn and can be singlehanded without difficulty. In general, the faster the small boat, the less forgiving it is.
For speed and ease of sail, a small trimaran such as the Weta may be a good option. It is fast, easy to single hand, relatively stable and forgiving, and can be beached or trailered easily. But there are many others that fit those specifications as well.
Saginaw Bay, Michigan
"The pessimist complains about the wind; the optimist expects it to change; the realist adjusts the sails." - William Arthur Ward