Any Tips?

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   I am a 16 year old guy with
short/medium length and extremely wavy/curly hair. I have to straighten
it daily, for it looks terrible if left slightly curly at all. Right
now it is at its longest, and i am getting it cut very soon. I want it
to lay straight down, and do not want to mess with it in any other way
than just straightening it. (ex. permanent straighteners, gels, creams,
etc..) when i first started straightening it about 4 months ago, I was
able to finish fairly quickly with great results. But recently, it has
taken much longer, with much worse results. I don't know if this is
dues to my hair being much longer than usual, or if its the irons
fault, i don't know. 

The current straightener I use is a "TI
Titan Miniature Styling Iron", with a 1/2" iron width seen here:
http://www.sallybeauty.com/Mini-Flat-Iron/SBS-152803,default,pd.html

Here are some before straightened, still damp, and unbrushed:

(click for larger view)

And here are some before straightened. But completely dry and brushed (gets increasingly curly and frizzed from this point on):

And here are some recent pictures from after it's straightened (at its longest) :

Sorry for the picture quality (camera phone)

It would be very helpful if anyone here could help me with any of the following problems:
How to explain how i want it cut (I have no clue how to explain it)
How to let it dry (air dry, blow dry, when to brush it)
Tips for straightening
A new (narrow) straightener
I can no longer make it look as good as the last set of pics, so anything you think might help
Thanks in advance