RE: jp 111 vs evo 90
It will depend a lot on your technique, weight and sail size. In short, the less refined technique, the heavier and the bigger the sail, the more advantageous the 111 liter freestyle board will be. This goes for flatwater and on the way out. Once on a wave the EVO will plane super early.
For me at 70 kilos and using a 6.0 sail or something, an EVO 90 gets going pretty much as early as a big freestyle board but it requires more work in doing so.
The reason for getting an EVO will be wave riding. If you're into that the EVO will simply blow your mind. It just makes people ride light wind waves better. You pay for this magnificent riding capabilities by having to work more to plane early.
If you want something that rides far better than your JP freestyle but still also is easy going wrt planing and stuff, you could look into the new Kombats. They have real wave rockers and hold a rail in fast turns exceptionally well, but are not as easy to rip on in smaller waves as the EVOs.
Tell us more about the conditions, how you sail, your weight, sail size, other boards etc and we may be able to give a bit more specific advice.