Word, Excell, and powerpoint are very good about at least the simple files being compatible across versions. I do not know why they did not do it in 2008

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You should check if the time is negative. If so show an error that clearly explains that negative time is not allowed and why the time the user entererd was negative. Then highlight one of the times in red

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You can use other installers for your service. I use Wix for mine.

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Go get one of those space heaters

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You could check out www.hotscripts.com or google "PHP photo sharing" or "ASP photo sharing". If you want to write your own solution and IIS is a limitation. You could use Tomcat or Apache and write a PHP scripts to do what you want.

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