JB,
Your weather is exactly what we experienced here this year! More rain than usual and unusual out-of-season cold spells... really cold spells. In fact, we just had night temps in the low 50s just a couple weeks ago.
I've done cherry tomatoes in our shaded hoop house, but they are never very abundant. I've accepted that it just isn't going to work out for us for many reasons. Just can't seem to make it work.