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I have Debian Lenny, since it's stable most of the packages are rather outdated, example being SQLAlchemy 0.4, whereas the current version is 0.5.x. I'm wondering if I should go with setting up backports ( if so how should I specifically set them up so that just individual packages I choose are upgraded ), or make it sid so I can grab some more up to date packages.

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What's your server being used for? How much do you value stability? I think this is really only a question you can answer for yourself. –  natacado Nov 11 '09 at 8:25
    
Another option may be to use ubuntu server. It is very similar to Debian and tends to be updated a lot more frequently. –  Zoredache Nov 12 '09 at 1:18
    
Ubuntu? Yeah if he wants RC and beta software on his server. –  Mark Stahler Nov 12 '09 at 12:25
    
It seems like a good compromise would be to use testing instead of unstable. Why is that not an option? –  Samuel Edwin Ward Mar 30 '12 at 19:34

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up vote 2 down vote accepted

If you're capable of building, backporting, and maintaining your own package tree, then go with stable, because I can almost guarantee that some of what you want won't be backported already. Otherwise, go with sid and only update when you need to (and keep a careful eye on updates for security advisories).

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