Making 1000 pages with 1000 photos???

Greetings
OK, it probably isn't 1000, but a whole bunch.
The Setup: See, I'm making a website for a friend who is a painter. He has many paintings, which are divided into different galleries on the site. In each gallery (landscape, figure, non-objective, etc...) there are thumbnails for each painting arranged in a grid. Each thumbnail will open a new window with the painting and a bit of info.
The Questions: What is the fastest and best way to create all these pages? I will need to Ps all of them to optimize and get some relative sizing, but almost none of them will have the same exact measurements. Perhaps Ps can do it instead of Dw?
I realize I can just create a basic template, and then will have to change the info for each, but I'm just wanting some speed tips if anyone has ever done something so ridiculously manotonous.
Please help.
Thanks.

I realize that... but the customer is always right.
I showed him several other things, but this is the way he wanted it. He wants people to be able to view and compare different painting at the same time.
I wonder if there is an easy way to make one page, but somehow pull the image and info dynamically? And then if they click another image it will open another window? Anyone do anything like that?

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http://support.apple.com/kb/HT4486
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Because it saves the battery on your camera
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Making 1000 pages with 1000 photos???

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