TomT wrote on Apr 25
th, 2019 at 2:54am:
Once committed to going in rough water either coming right at you or from behind it's near impossible to turn broadside and escape to the shore. I'll take rain over wind any day.
I spent a large part of my morning looking through old shots for PODs (since we're out) so I'm in a paddling state of mind and am willing to say a lot depends on the boat, the paddler(s) and the reason for pushing common sense limits.
I'd almost always rather paddle into a gentle breeze than anything else - unless it's cold and raining/sleeting. That said, following seas... I'm rarely a fan and I'd always prefer a bigger boat with more freeboard. Once you commit, you know damn well it's only going to get worse. For a long long time I noticed that when I actually put on my PFD, it meant I felt I was paddling in conditions beyond my abilities. Either that or the bow paddler didn't like paying attention and had a propensity to take air-strokes once in a while.

Plus looking behind you for swells is not all that easy - for me at least.
I remember once being windbound (solo with my tandem) and thinking well, at least there's a campsite downwind. If I misjudged or efed up, chances are me and all my stuff would all wash up on a sandy beach. It was a warm sunny day so I put on the PFD, called it a learning opportunity and a took a chance. That was a tandem paddled solo. It was fine. Good thing because the site turned out to be occupied. They politely waved. Bad because that meant I had to re-aim for a chute that had shallow rocks I had a hard time missing. I knew I could stand by that time so that was comforting.
Another time wind direction and landing conditions made it hard to launch a borrowed Prism with all the waves crashing but once I got away from shore it was doable in a smaller boat. I could only paddle straight into it because quartering meant water in the canoe but at least I could make progress and things would get better so eventually I could get to where I was actually aiming to get to. I'd never paddle a big trough with that boat. I tried in safe place. Oh that was dumb and I knew better but then I knew for sure.
Another time, when I borrowed a Magic, I wanted to go down wind and knew it was an awful idea with that boat. But since that Magic seemed to me to love the troughs, I could make my way sideways to an island a little farther northeast where I thought there could be less wind. A couple hundred yards into it, I could no longer see the upwind horizon sometimes. Well that was stupid wasn't it Dave? I picked my battles with swells and by time I reached a level of confidence I also reached the island and things had calmed down to the point that following seas weren't a problem so I had a well deserved smoke while drifting and taking off the PFD.
Round bottom, flat bottom, balance, freeboard... it all makes a big difference.
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A long long time ago, a little before I started QJ and the web was mostly all helpful goodness, I stumbled across a quiz of sorts. It had a map of a lake with long stretches of open water and islands and wind chutes and stuff. The questions were something on the order of if you were here and you wanted to get there and the wind was coming from wherever... how would you get there? There were things I quibbled with at the time but thinking back, I assume 'canoes' were all tandem aluminums with two paddlers. It was really good food for thought in any case.