that doens't have much sense to upgrade to the outdated versions. you should just grasp your balls and start an upgrade to the latest one. it will take 5x more time to upgrade it version to version. what sense is it to upgrade to syntax and functionality that is outdated and then to rewrite it again and again. install new version and go ahead fixing things! dont be a pussy.

Some of us place more importance on catching bugs and keeping our product working than on proving our masculinity.

Also, in general there will be very little of the "upgrade to syntax and functionality that is outdated" - while a lot changes in a standard Python/Django release, I don't think there's much that changes in two backwards-incompatible ways in three releases. Most of it will be adapting to one change at a time, which may touch the same line of code more than once, but will not waste much effort and will give you a good idea of what mistake you make when you make it.