Just to add to the discussion, as I bought a new boat last year.
On the making things easier front, a couple other things to keep in mind.
1) Even though mine did not, my understanding is that new boats now come with the trampoline double grommeted up the center, making it "easier" to get the trampoline stiffer.
2) New boats also don't come with the adjustable jib halyard set up on the mast, as seen in the picture on the HCA website for the Hobie 16. Below is a link, and the picture is at the bottom of the page. This set-up makes it "easier" to get the preferred tension on the standing rigging for racing.http://www.hcana.hobieclass.com/default ... 0071/9268/
Finding a second hand boat can be a challenge, as there are not that many produced in the recent years in which a lot of positive improvements were made. If your looking to get into racing for the first time, then getting a second hand boat from a local fleet racer would be best, or if you've race before, then get a new one, its worth it.
When I bought my boat, the things I added to make it race ready were:
1) Neoprene the side rails
2) Add 6:1 downhaul
3) Double grommet the middle of the tramp
4) Add adjustable jib halyard set-up
5) Add a small "eye-strap" to the mast to hold the jib halyard close to the mast.
A good resource to check out "race ready" boats is to scroll through the gallery of the latest Hobie Worlds earlier this year in Australia.http://hobie16worlds2014.hobieworlds.com