I think that there is a lot of a personality component here. Is having a 2nd rate ski going to demotivate you? Personally, in my flatwater experience, I started out with an old, slow $350 beater K1 and learned how to paddle it decently. When I traded up to a good boat, I really appreciated it, and it was motivating to be able to blow away my old time trial speeds. That said, if you have the money availalbe, why not get a nice boat right away? So you can go either way on this in my opinion.
