OP: Don't know if you've joined a Journeyman League, but I'm going to suggest looking at all your Warcaster options first. They will dictate how your game plays more so than your Jacks and infantry. If you can, go through all of Khador's Warcasters and find two that you like - be it rules or aesthetics. Warcasters are the hardest pieces to wrap your head around because they can put in a tonne of work, but also lose your the game. Once you have that set, it'll be a lot easier building an army around your warcaster.
If you're restricted to the Battlebox though, get Widowmakers first. Winterguard function best with the Unit Attachment, 3x Weapon Attachments, and the solo Kovnik Grigorovich.
If you're REALLY set on Man-O-Wars, you'll want the Iron Fang Kovnik to go with them, otherwise they'll just be too slow to matter.
A great investment in terms of learning aids for Warmachine is Warroom. $60 nets you EVERY SINGLE CARD currently available as well as future updates, alongside quick reference rules - or drop just $7 for the whole Khador deck (the longer you play, the more you'll want the remaining decks though).
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