If you want to speak substantively with and possibly recruit the Bolton, choose the Conversation to speak with him rather than the Action to spar with him, for two reasons. First, a spar only gets us a fight, against an opponent with an unfamiliar style, and goes to improving Prowess; as we saw with Harwin, it does not go deeper than that. Second, sparring at the same time as we participate in a tourney increases the chance of our mystery knight disguise being pierced before we're ready to dispense with it, while conversing does not.
This isn't about the people, but the actions, though. Training at the same time as entering a tourney carries an injury, risk, as laid out in the action descriptions themselves. And every plan is dead set on entering the tourney. Meanwhile, it's not that we overly love Beesbury, talking to him just relates to our promise to Isembard Arryn from last round, that's all.
Both of these are fair points and partly why I honestly prefer the Feast option most of all since it could net us (if it's anything like the Gulltown Feast)
three mini conversations. I, of course, want one of those to be with Rogar but that still leaves us with two more that can be filled by Beesbury and that'll leave us one free that can be taken up by one of our as yet unaddressed companions like Rhea or Redfort. Beesbury is someone we can speak to plenty when we get home and we've already been given approval by our Father for the Isembard plans. I'm sure we'll get something interesting from talking to him, such as finding out why he's in White Harbor at all, but it seems like a missed opportunity to not speak with one of the most important Northerners here in favor of someone we can just talk to at home. Rogar has been mentioned in southern tourneys before which I think is pretty unusual for an Old Gods following Northerner which I think is interesting. He could offer a new perspective on how other people view Tourneys and the classic knights we seek to emulate.
The Manderly's are worth their action no matter what and taking time for talking directly to them
might offset any slight given when we aren't 'seen' at their Tourney much as seems likely or their Feast at all if that's how things shake out.
I'll make one of my own plans including it since no one else has. Not my ideal one but I'll stick to my guns here.
[X] Plan: Getting Under Their Skin
-[X] [Conversation] Speak with Desmond and Medrick Manderly
-[X] [Action] Enter a Tourney as a Mystery Knight
-[X] [Conversation] Speak With Rogar Bolton
[X] Plan The Time Has Come
-[X] [Conversation] Speak with Desmond and Medrick Manderly
-[X] [Action] Enter a Tourney as a Mystery Knight
-[X] [Action] Train
--[X] [Duel] Rogar Bolton
[X] Plan: Tourneys, Merlings, and a Feast
-[X] [Conversation] Speak with Desmond and Medrick Manderly
-[X] [Action] Feast
-[X] [Action] Enter a Tourney as a Mystery Knight