Aight There are a bunch of factors as to what to buy. I currently ride Liquid Force and I am sponsored by Liquid Force so that is what i would recommend simply because those are the boards i get to ride. As for what you want to spend. If you are going with 500 and you want to get the best board combo for you....I would go with a 142-146 LF Trip with the biggest LF ultra boots you can find...probably a 2X. These are 500 seperate but I am guessing you could get a better combination price at like overtons.com, or places like that (I worked at overtons too). The Trip is a continuous rocker meaning that the bottom is a continuous curve and it will give you a lot of consistency in your jumping (pop) off the wake and the small cupped molded in fins allow you to ride the board loose when not on edge but cut hard when you want. Pretty forgiving as well. You can buy many different boards though...Hyperlite, Ronix, Gator, O'brien...they all offer good boards. PM me with any questions though and good luck
Here is a good board for a good price today. This website is legit. I have ordered a bunch of stuff
http://boardersbestbuy.com/