First of all, congrats on starting on the pump.. It has helped me tremendously!
As far as the cannula goes.. just take it out, rip it off.. no big deal there (I wondered the same thing when I started too

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I just have the clip on my pump (like to attach to the waistband, jeans pocket, whatever), and if I decide I want to carry it in my bra, I just attach it front and center.. it rarely shows unless the shirt is cut lower in front or if the shirt is fitted...
On a daily basis, I only carry a syringe and insulin in case something goes wrong. But, I also have the freedom to leave work at anytime. However, if I am traveling out of town for a prolonged period of time, I will take one of everything... just in case!
I do check my blood sugars the recommended before and after meals. If you're high after meals, check too see how much insulin is still active.. (meaning in your system..) You can do that by starting the bolus procedure but entering no information.. when you get to the "estimate details" screen.. scroll down to the bottom and it will show you how much insulin is still active.. if there's nothing there, go ahead and correct.. this step saves you from giving yourself too much insulin and from potentially going low
Good luck with everything and enjoy your pump!