I've put up both hardy 4'x8' sheets and the plank siding.
If I recall correctly, those 4'x8' sheets weigh over 90 lbs. It's fairly easy to put them on at ground level, but I would not want to do so 2 floors up. There might be some equipment that can be rented or some clever working methods I haven't learned or thought of to make it easy and safe for 2nd floor work. You would have to check on that. (And report back what you find if you do! :) )
The planks are really easy to work with. Buy a pair of these
http://www.ebay.com/itm/like/151259434767 . I think you can find them a few dollars cheaper if you look around. The first two (the bottom two) courses of boards will take a little bit of effort to get them to go on horizontal to the ground. The top-most board overlaps the one below it by about an inch. (I forget exactly how much.) Once the 2nd course is on you can start using the clamps. The clamps hold the next board when and where you need it. All you have to do is hammer it in. Remove the clamps, move to the next spot, and repeat. You will find that everything that is within hammering range of the ground will go blindingly fast!
I did much of this by myself and the 2nd floor portion (thankfully small on the house I worked on) went much slower. That's because I had to climb up and down the ladder two to three times for each board. If I had a buddy working on it with me it would have more than twice as fast since we would not have had to spend as much time going up and down ladders.
As for tools, aside from the Gecko clamps, you'll need a strong utility razor knife, preferably with titanium edges and a straight edge. You score the board on one side and then snap it over a sharp table or saw horse edge. A strong pair of pliers lets you nibble away any bits that didn't break clean. You'll go thru the blades fairly quickly.
A jig saw with a bunch of blades will be needed for cutting boards to fit around windows, doors, etc. You'll wear thru those blades fairly quickly.
A drill with a concrete bit if you need a hole for a cable. And, of course, nails and a hammer.
You'll save a bundle if you do this yourself. You can work on a wall segment at a time so you can split up the work in weekend-sized chunks.
Hope this helps.