RE: picking a tree stand
Fly-- What do you know about the area you'll be hunting? Where do the deer bed, where do they move to feed? What are the food sources that will be available at the beginning and throughout the season? If you know these things and can establish a general travel route to and from these areas. The next thing to do is find a suitable tree for your climber. Make sure the tree is not just out in the open, where you may be silhouetted against an open back ground. (from the approaching deers point of view).
If you are unsure of these things take a walk now..see whats out there, any sign still from last year rubs scrapes, any tracks from recent movements?
As summer begins to wain, scout from a distance with binoculars at first and last light. See what you can learn.
As Jeff said play it safe at the beginning better to error on the side of caution and ease in. Unless pressure dictates that you hit the best area as soon as possible.
Lastly don't get pinned down to one spot have multiple spots and rotate them, often, over hunting a stand will turn a great spot sour rather quickly. Always hunt the wind and remain scent free as possible even from a treestand. Good Luck.