You can do it of course (we have) but you're fighting the elements. No matter how nice the weather is, there's not much you can do about the fact you're sitting in 40 some degree water.

On the other hand, October is waaay better than May. Then that water temperature dynamic works in your favor nicely.

On the black flies, I've seen a few in town this spring which is rare along the coast. As wet as it's been, that tells me they will be brutal inland this season. Mosquitos will take a few weeks to show up here but they're never that bad. We rarely need screens on our house in the summer. Inland, a different story.