I would tentatively say yes to both, what I can tell in place of maneuvers the swordsages learn spells and they are<em>cast</em>like maneuvers, however I would rule that at that point swordsage levels count both as initiator and caster level and the 'spell maneuvers' he does count as spell-alike abilities than regular spells (so 'spell maneuvers' can be dispelled by a caster). So in short they qualify and windwright captain progresses swordsage levels in regards learned maneuvers or initiator levels in same spots where spellcasting progresses.