Sunny,

You're price of $2K for boat and $2K for "supporting equipment" and then money in the bank for upgrades has just busted this wide open for about 50 more posts and lord knows how many other different boats.

Since you have access to people who can get you started, to show you the "techniques", buy a boat that YOU are excited about. All choices are going to involve a learning curve and you'll end up making mistakes (hopefully not too costly) and learning from them. If you buy the boat someone else is saying is "best" for you, and you have reservations...well, we know what will happen. I'm so glad I did not by that Laser and opted to learn how to sail on the H16 years ago. In about 2 months the Laser would have been too slow.

Look at some portsmith ratings of suggested boats in your price range, ones that sparks YOUR interest, and go for it!