That's what temperature compensation tables are for.
People point fingers at those for being pretty bad - just a devil's advocate viewpoint.
I'd say if you are gonna tune in the winter, don't make it too aggressive of a tune. If it's in the summer, you are in a worse case scenario. I still wouldn't bother with two tunes, just keep that in mind. The car will compensate for the differences though for the most part.
Also, if anybody is running e85, you a lot of times run seasonal tunes to make up for the different grades of e85 throughout the year.