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Definitely worth testing out, I suppose, but I don't think it will end up being the case.
I've haven't specifically considered this effect from readied weapon icon, but I do adjust my readied weapon icon around a lot, usually to change the "relative strength rating" color of the mobs at a certain location.
However, I preface everything these days with the cautionary note that we have recently lost a huge percentage of available flagships. Unless anyone can say they've seen the Navy Bulwark, Panther, Greyhound, or Centurion flagships lately; or, perhaps the EITC Ironwall? All that is left is the Colossus (Dead Man's Trough/Isla Tormenta), the Barracuda (primarily attached to Brigand Bay/Isla Perdida), the Man-O-War (Smuggler's Run/Kingshead), the Kingfisher (Scurvy Shallows/Rumrunner's), the Corvette (still primarily around Outcast, but with more tendency to use its entire travel range), and the Sentinel (your guess is as good as mine right now...it can usually be found near the seam between the Leeward Passage/Dead Man's Trough/Isla Tormenta, but I think it might actually still respawn in Boiling Bay).
In any case, I have always boarded the highest level Navy ships after putting my doll in the readied weapon icon (I also regularly take out opposing high-level helmsmen with grenade on long volley while still on my ship...although I admit its a waste of coin). I was into my 20s before I really sailed with a crew, so I use to say that was my crew...my first mate Dolly, and bunch of wee round lads from Singapore. For me, though, 17 Grenades are one of my higher skills (23 Sailing, 20 Cannon, 18 Dagger are higher) and 15 Doll is my 2nd lowest (only 5 Staff is lower).
Finally, I have always seen that sort of variety for each level of flagship. In fact, I sometimes have had trouble figuring out exactly how the game is determining what level to give a ship; I often saw higher level crews and better loot from level-18 Centurions than I did from level-20 Centurions. An even better example of mine would be the Man-O-War because there were many times when I'd swing over to meet 5 level-29, so many that I just got in the habit of readying the Doll before going over, and yet there were still times I'd swing over to find extremely low level crews too.
Things may have changed with the 30 April update, but my best guess would be that it doesn't depend on the readied weapon icon. I'd be willing to do some testing of it tonight, when I get on, and I'll report back what I find out.
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