are your client/user/development machines out of sync with each other? it seems part of your problem is geting a standardized environment. support can be very hard if everyone is running different versions of xyz module.
once your shop can agree on a standard environment, answering the other questions should be easier. upgrading for the sake of upgrading has kicked my ass more than once, so get your dev crew together and find out what the needs are.
once you guys agree on the standard, you'll have some fun getting the dev group upgraded/standardized. once that mess is sorted, you'll have the experience needed to tackle this on your end user machines, production servers, etc...
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