Yes I got water in my middle ear and it was not fun. It got infected and I was remote (living on a sailboat) with no medical care so it was just my wife (nurse) and some antibiotics to get me through. Luckily no permanent damage.
I am good at managing risk, I just want to educate myself to reduce risk to an acceptable level. Like I said, probably just shallow dives and pro-ears with Doc's Pro Plugs to catch splashes of water if they get in the ear-cup while I surface immediately. I don't dive with paid tours and groups, just my wife and friends so no pressure to go deep or continue with the dive if some water gets in my ear cup. The Pro-ears are pretty reliable if used properly.
Your risk management is for you to decide. I obviously had my reasons at the time to do what you describe. I found the ProEar mask to be reliable, but not 100%. Being bald helped! Good luck, I hope it goes well.