Your other option is to have an upholsterer do them for you. They will have the materials, tools, and know-how to do this easily. They also know how to line up patterns such as stripes or plaids. Most upholsterers don't charge a lot for chairs. One I know does them as a sort of loss leader to fill in his time and gain future clients.

Thanks, Bob's nephew. I'm aware of this option. My local shop is NOT cheap and I doubt highly he'll take a loss on any transaction. Based on the number of pieces I see in the queue, he's not hurting for business.

The ease is determined by the construction of the chair. I have never recovered a chair like that before and I can't quite tell from the picture...

As far as how much fabric is needed. Take the fabric off by removing the staples, assuming that is how it is made, and measure the existing piece plus an inch all the way around. Than add them all up. There maybe be another way but this is how I do it.

The people that work at a fabric store can probably give you good info on how much to buy. Just come with the old fabric for reference. I love the ladies at my local fabric store. They are so helpful and give me lots of confidence!