I'm same here, having hard time choosing a board, but I think I'll end up on Jamie 2015 as I'm more on boosting, sisy kiteloop, free ride and a bit of wakestyle. Sbend, backroll and 313( i always miss the pass) :)
I tried a couple of board like Axis Vanguard(nice board, find it a little bit stiffer than Jamie and didn't like it on chop ) ,
Naish Dub (which took time to get use to but has a better pop than the other boards I've tried and easier on chops, less spray on the face but hard to go upwind unless well powered ),
Nobile NhP ( Dint like it as it feels a bit flat un-like the Dub)
and Jamie 2014 which I'm currently using now ( I like this board, lighter and easy to throw, enough rocker, decent pop and a easy to go upwind).
Thinking of Gambler but I feel a bit old to be doing wakestyle trick as I'm already 36 :)

You'll notice that the name Shinn keeps popping up here.
The North Jamie is an epic TT but they are so small you'll lose upwind in challenging conditions, ie, low wind or strong currents.
I am wanting to have some of what Skywalker is smoking because everyone here is coming off the motions and hopping on the Monks and
King gees for the smoothness. Definitely no com petition in chop eating here. The motion is a great TT and makes moves so easy but it is very
direct and is a bone shaker. The Shinns will do all the tricks it's just you have to get used to the timing which is a little different as I find they are
a little slidier and require a diffferent feel. The landings are so much better on a shinn. The 2012 chopstick by cabrinha will eat chop but not amazing for
moves. The Mako by Ocean Rodeo is uber smooth and rides toe side as easy as heel side. I would go the 150 its got the same surface area as most 138çm
TT's . you can do all the tricks but it's a bit heavier and you probably won't go as high but you can surf anything on this. Just so much fun and zero spray in the eyes.
Basically you can't get everything in one board. Like glenndog said, more rocker = better tricks but less upwind so that means less time for tricks. theré's always a trade off.
Demo and borrow till you find something that clicks for you. I would steer clear of Tona I had one a few years ago and the build quality was garbage, in fact that's where it lives, in a dump because it fell apart in a couple of weeks. Go with reputable brands that have been around and that have some sale centers around that can get you parts or sort warauntees for you.
The new Shinn sneaker pads have fixed all those problems mentioned in this thread. They were definitely an issue. I ride all my shinns with Cab Sync or SS Joints but the new ones the rest of the crew round here are on have the sneakers and they definitely rock and don't let go. They are better than the Naish ones which everyone was raving about last season, & justifyably as they are awesome.