welcome to fly fishing!
hey that shakespere walmart special is what i learned on, so, its definatley do-able, but, once you get the casting down, you will want to upgrade,. my advice is to just go out in the yard and put out a target, and just keep trying to hit it, and increase your distance. the way a flyrod works is it uses the weight of the line to flex the rod, and thats where all of your power comes from... the thing that took me forever to figure out is to let your line extend all the way on the backcast before making your forward false cast and to let the rod do the work. you will be amazed how little effort it takes to cast when you do it right.
i have a fly somewhere (thats now retired) that i fished with every opening day of trout season, and its caught close to 100 fish, so, if you make your fly right, or take care of them, you can get alot of life out of one.
as far as flies go? wooley buggers