I started a few months ago with a Super Cub, and its a great first plane to have! I have flown it in winds of up to 15mph and it's coped well, and don't let anyone tell you it can't do aerobatics ;-) I've since gained a Wot4e and a T-28 too.......
With regards to simulators....the best experience is going into the great outdoors! I found there was such a difference between a sim and the 'real thing' that i am unsure as to whether it's an advantage or not?!?
Have fun and let us know how you get on!
Claire