Every type of boat is different but most leaners will out point most cats. So the real question might be, do ya wanna point higher or do ya wanna haul butt?

As far as recommendations, you can't get a boat that's any simpler to sail than a H16. If you want boards take a look at the H17 and TheMightyHobie18. The H20 has a bunch of stuff to do for set up but it screams once it's on the water. I'm sure others will chime in with their recommendations.