Rope - (most important piece of gear. after all it is what connects you to the boat and allows you to shred all day.)
*most important is to make sure the rope is made from "dyneema" or "spectra." these are premium no-stretch materials. brand is kinda preference, but straight line having a shorter "main line" than other brands is kinda nice. ("Main Line" is the longest portion of the rope.)
* get a rope with longest total length you can ie. 85')
*having a PU plastic-like coating is really nice as it allows the rope to glide through fingers.
*get a bright/ light color rope so it is easy to see
Handle - if possible try a few grips in the store and see what is most comfortable. have someone pull on the other end to simulate some resistance.
* many people are really digging the suede and leather grip handles.
* consider a "cheater grip" -- this is a smaller handle a foot or two down the line from the handle itself. this is used for wrapped tricks where the rope is partially wrapped around the rider to help in spins and grab longer.
Boots - (2nd most important gear. you cant enjoy your board unless you enjoy the boots that are connecting you to it)
* Definitely try some on at a store first. move your body around and bend into grab positions to see if you want a stiffer or softer boot.
* most prefer closed toe boots, but you may like open toe better, especially if you are sharing the boots with someone with a different size foot.
* Velcro straps or Laces?
* because you have a snowboarding background you might like the idea of Hyperlite's new system binding and boot. the boot and binding are seperate pieces as in snowboarding.
Board - because you are a snowboarder you may (but not indefinitely) like a board with some flex and that was built more like a snowboard in materials. often these boards are known as "flex boards." these boards are described as: soft landing boards, have stored/ load energy kind of pop, eay to press and slide on water or rails... but not all will agree with these claims
the ronix phoenix is one such said board
any board from the brand, slingshot would qualify, obrien paradigm, liquid force team shane or watson hybrid, and many more.
* try a "hybrid" rocker board, most boards are and have switched to a blend of both worlds. look for rocker names like: hybrid, subtle 3 stage, abrupt continuous, etc.
* Might consider a board with bolt-on fins in each corner (minimum of 4 bolt on fins) this way you have more freedom to play with how the board rides by changing or removing fins.
Life Vest -
cga vest all the way personally. neoprene material of course. try before you buy if possible. should be tight, but not to the point that you can’t breath. remember that the vest will stretch a bit, especially after wet.
board shorts (give CIRE boardshorts a try http://cirewear.com/
Wakesurf - no experience there, but gota do it some day
*wake surf rope - get specific rope for wake surf. heard of some lost fingers using wake ropes as surf ropes
Wakeskate - not so much experience there either
sorry if this is a little much...before i go to far I will try to answer your question about rocker and what makes for a soft landing board
Unfortunately there are many different theories of what makes a soft landing board, but there is no unanimous agreement. just another area you will have to form you own opinion.
Continuous rockers generally do have softer landings (maybe not significantly) than their threestage counterparts. but there are other things that contribute too.
some believe in belly spines and other bottom features to break-up the impact. others think that a smooth featureless belly will prove to have the least resistance and glide on impact and be softer.
How much a board flexes and if that is good or bad is another endless argument.