Against my better judgement, previous experience and suggestions from all the previous posts on this thread, I am going to try my strawberry pot one more time!
I have dormant roots this time, so if I have to grow them as annuals I can harvest right away, since I am thinking they will not survive the summer.
What should I put in the top of the pot? Definitely not a strawberry!

The top gets way too dry for that! I would like to plant something that can tolerate full sun and frequent watering, will possibly provide some shade for the pockets and will play nice with strawberries and spinach.

A tall order! I was thinking of oregano, since it was suggested before. Will it be ok with strawberries though?
And any suggestions as to the best materials for even watering? I was thinking about maybe some PVC with holes drilled in all around? Or would the water just all drip to the bottom? Maybe just a frozen water bottle in the top?