Not to take away from your question, but I found a similar question in /r/asklinguistics that my be interesting: Was there ever a point in time where “you” and “thou” were pronounced with the same vowel sound?, where /u/hrt_bone_tiddies thinks this is not the case. I am also pinging /u/macnfleas because he seems to be a linguistic historian.

I asked the same question myself a couple of years ago, here is the thread with responses by linguists.