It all depends on what you want you sailing experience to be.
If you race then you are going to want to be on the boat that is being raced in your area. If it is portsmouth, then sail what fits you. Cost is relative: if you only paid $500 for a boat, but never use it, then it was too much.
If you want or need "bullet proof" then do not get into racing catamarans. A colission is going to do damage. If you want to drag a boat over rocks and sand, you will damage the bottom of any flat bottom design, 400 lbs or not.
All boats also have limitations. If it is blowing 35+ there is no cat I would rather be out on than a H16. They are not nearly as much fun in lighter winds though. My F16 has less upwind sail than the H16 but is high aspect. has a spin and a lightweight platform. This makes it a blast to sail in pretty much all conditions until the dog goes blowing by. Sailing the 20's and 18s is fun, but a lot more work and the feel is not there. They are not appreciably faster and much less responsive. Would I want to do a Tybee on the 16 or the 20....20 hands down, but to go out and sail for an afternoon, or run around the buoys, the 16 is a lot more fun.
The other boat that keeps getting bashed is the A. I like to sail with crew. That is my only complaint about the A. There is no boat that teaches you sail like the A cat. Every adjustment crew motion etc. provides instant feedback because the boat is so light and responsive. 1 sail and light weight, it is easier to get on the water than a Wave. It is a minimalist boat with flat hull bottoms that is relatively expensive, of course you are going to try and treat it with care.
Light weight increases the cost to build but definitely improves the sailing experience. What value that has is entirely up to you.
