Hi Jimbabarino,
The trim strap you speak of has two loops, the p[urple one, which "powers up" the kite and the black one which "depowers" the kite.
The 14 Halo is a hell of a jump up from the Pilot, kinda one extreme to the other. The 14m Halo is a big bitch which is slow, heavy and cumbersome, but it has bottom end to burn. Coupled with the right board, say an Airush Exile of 06 or Protoy Exile of 07, it should get you planing upwind in 11 or 12 knots no problem.
The Halo's are technical in that they develop heaps of apparent wind power or dynamic power. Build up some speed first before trying to go upwind. Once you get moving the power comes on in spades. If you just park it and sheet in waiting for it to happen, it wont be as effective.
I rode the 10m and 7m Halos all last year and still ride them from time to time for pure jumping bliss.
They are very technical and very high performance, I would have said way too technical for a beginner to extract the performance.
A friend at Pinnas has replaced his 19.5 Lift Pro with a 16M and 14M SLE Flow and reckons they have more performance and bottom end and have a easy ride to them. I also ride the Flows 7, 10, 12 and 14 from our rental centre and they are a pure no brainer and are really fun.
I hope this helps,
Good winds,