This is just food for thought, but Jerry Bernard thinks through the order of Paul’s letters in a different way. I like the fact that he explains why he initally thought one way and then why he changed before demonstrating his reasoning.

I don’t agree with some of his conclusions on other topics (Things that ended in the first century), I don’t even agree with him on the timeline of Paul’s letters. However, it isn’t an unreasonable approach and so it deserves some consideration.