There are lots of good deals in the states all year but the fall is the best time to get an absolute bargain. Check out this: type in sitemash crestliner for example into a google search. You will find a site called jaxed that will hunt out every crestliner listed on ebay, craigslist and kijiji in North America - newest listings will be at the top and you can narrow your search to include key words and even by state too. that is how I found my last 2 boats. I bought my first crestliner fish hawk in Michigan and sold it 2 years later for a profit of 2500 bucks (including travel costs...). I just bought a 2007 1600 fish hawk with a 75 optimax (with 20 hours on it and extended warranty) for 11, 750 (taxes, travel... included). It is a new boat practically and it is still under warranty. You need some key paperwork, the trailer must not be recalled, and you pay 13% tax plus a 205$ trailer fee and that's it! Lots of boats in Michigan and PA.
I just looked every day for a while and pounced when I saw an opportunity. As long as the dollar stays strong it is a great way to buy. Your best bet is to find a model you like and then stick with it - that way you can compare apples to apples. Lund (may be too pricey for your budget), Crestliner, Alumacraft and Princecraft are all well built aluminums that hold their value better than most. I would stay away from Legends or Trackers as they do not hold their value as well. PM me if u need more details re paperwork needed...
Landry