I've not watched them in chronological order... Of any sort in fact. I feel like I might try this though there's been so many blogs and books that have done this I could probably read them and pretend I did 😛

It's not established fact - nothing is. We could be watching edited highlights from the Matrix where The Doctor is deliberately making himself look good when in fact he's a complete tool. Assuming that isn't the case, I think it's fair to assume what we see on screen is chronological from The Doctor's point of view - the whole River Song thing would seem to confirm this for the new series at least. In 'Web of Fear' they mention seeing the younger Jack Travers from 'Abominable Snowmen' a few weeks ago for instance, one of several times characters refer back to previous events...