RE: Board quiver advice for an intermediate
I know you're wanting Roger's advice, but your quiver is so similar to mine & at 185lbs I'm similar weight. I can maybe give a little extra info & hopefully be somewhat inline with what Roger says.
I agree with Roger's more detailed suggestions. For example, I kind of wonder if I will change my 135l freeride for something like an Isonic. It's hard to really know until you've tried what you have in your local conditions for awhile. I personally think your board selection is quite safe.
My comments on your wind range (I assume your sails are fairly good & modern):
12-18 knots C33 8.5 - Yes about right
15-21 knots C133 6.7 - Yes but if the wind is steady, you could switch to the Kombat
18-24 C133 5.5 - C133 will probably feel too big unless the water is really flat, Kombat on 6.7 or 5.5 would be better
21-27 K95 5.5 - Yep - this is where it rocks!! Give that sail some downhaul.
24-30 K95 4.5 - Yep, but at this point the board may start to feel big, especially in the upper 20's with big gusts & freaky great ramps in the swell. That's why I'm looking at the Acid 80.
I've found the Kombat works best with footstraps outboard. This will be a must for the 6.7 sail. For higher wind, inboard allows more control when overpowered & works very nicely, but, in my mind a bit les than ideal.
Hope all this helps.