Don't really have any answers on your question about Paul. Just being honest...
However, I think it is commonly accepted that we don't know for sure when Revelation was written. I don't think we can go so far as to say we "know" it was written in or around 95 AD. Although the predominant feeling it was written in that timeframe.
Here is a thought on Paul. It is clear that the Lord himself taught Paul.
For I neither received it from man, nor was I taught it, but it came through the revelation of Jesus Christ.
Thus, it could be said that Paul, if he was the first church age messenger, was instructed by the same one who gave John the revelation to write down. Thus the message, to the messenger of that age, could have already been delivered to the messenger and then recorded for all time in Revelation 2. Just a thought....
Another question around Revelation 2-3
I would say from the text of those chapters that "a messenger" to each church is clearly stated. I see no other way to read and understand "To the angel (messenger) of the church of Ephesus write,..."
I am just looking at this from a bible student perspective right now...
What is meant by "angel" or "messenger"? The text reads pretty plainly that each section is addressed to a single messenger.
If there is a messenger to each church, was it an age or an individual church? I honestly can't see how this could be written to a single church in that day.
If it is an actual messenger, then how would he deliver that message to the church or age?
Is it intended that he deliver the message himself, or is it just delivered in the text for all to read? (if it was just intended to be in the text for all to read, then it would be somewhat odd that it says "To the angel of the church..." as one would start a letter to a someone.
These are just interesting questions whether looking at it from a message perspective or not. I have a Thompson Chain study bible that outlines "church ages" as well... so this is not just a WMB view that it could mean ages.