About Masamune, such information is available in the "walkthrough"... which is more of a character collection guide than an actual walkthrough.
http://alicesoft.wikia.com/wiki/Sengoku_Rance:Walkthrough
One Eyed House
* Territories
エゾ (Ezo), 奥州 (Oshu)
* Basics
o To declare war on them, you must first do the ??? event in their territory. Then a new event battle should appear in Saitama. After doing this battle, you can declare war on them.
o After taking over the last One Eye territory, there will be a duel between Rance and Masamune (with Sill supporting Rance if she is available). Masamune will heal himself to full health using eyedrops whenever he drops under 50%. To counter this, first recruit Nogiku, Orime, and Noir, as well as defeat Omachi's unit in battle (and trigger the event after battle), then pick a Purple Event in the One Eye House territory to learn from the three girls how to fight Masamune. If this event is triggered, Masamune will still use eyedrops only once, but subsequently that move will be disabled by Rance and Masamune will no longer be able to heal.
o If the Tokugawa House is still standing while you are fighting the house (Regardless of it's affiliation), at some point, One Eyed Masamune might take control of it.
* Noteworthy captains
o One Eyed Masamune - Will join you randomly after you defeat his house
+ In 1.04, he will not join if any of Nogiku, Orime, or Noir is cleared (originally he could join even if all three girls are cleared)
+ will not join if you in 56 route (but it is safe to recruit him first then enter 56's route)
o Omachi - Defeat her unit in battle to get an event where she turns into a stone. Then after Masamune joines you, get Masamune up to Trust, and then an event should occur where she joins you.
o Nogiku - Defeat her unit in battle, rather than just winning the battle. Afterwards, she will be captured.
+ Requirement! You have to recruit Akashi Kazemaru who MUST have Hibachi as his passive skill.
o Orime - Defeat her unit in battle and she will be captured. Requires a ninja (Suzume is enough).
o Noir - Defeat her unit in battle and she will be captured.
Just a note, I was able to encounter fight three of the girls by repeatedly attacking a zone (not a castle) in the southern territory and reloading if they didn't spawn. Omachi, however, never spawned in the southern zone after like 20 reloads, but I ran into her right away in the northern zone. Makes sense, since she's the Guardian of the North. Likewise, I'm betting can't get the "Guardian of the South" in the northern area. And about that requirement that you have Akashi Kazemaru with Hibachi- it's only needed that he be in the army, he needn't be part of the fight.
So a few other comments- I may or may not be done with this game. I thought my hatred of Rance couldn't get any worse, and then...
I completed Ran's path with the Ran character-clear. I really hated that she stayed with Rance. And I thought she was like the only charcter with some integrity. At least she stays true to Soun if you don't boost her relationship; sadly that's kind of a hard thing to do given the easiest way to character clear is to get everyone in your party then use satisfaction to raise everyone's affection level.
I really don't mind the spoils of war raping and pillaging, which is actually really funny at times. However, I can't stand that he's still such an ass to his companions, what with all the lying and raping that somehow endears women to him.