In reply to MisCon
Sun and Emerald
Vol 1-3 Cinder and Ozpin
"Arrrrr, private MisCon, welcome to me arrrrrrrrrmada!" Masterweaver chortled at the man, looking over the husks with a discerning eye. "And what beauties ye have fer me today, eh? A vessel from the thieves' company, and--ah, an eternal flame engine, rare find that!" The black robe pulled out a wrench. "Should be easy enooof ta patch these wrecks--soon as they be afloat, we be shippin' out fer our first raid, savvy?!"
Sun and Emerald, Emerald and Sun. What do we know about them?
Sun's a fun-loving kind of guy, willing to stick his neck out for his friends. He's known for his abs, his somewhat dorky personality, and his ability to pull surprisingly deep observations and philosophy out at crucial moments. He's demonstrated a disrespect for law--although he has a deep respect for friendship and is easily willing to play along with legality if it means helping others. He's brash and outspoken, brimming with confidence and always, always seeks to do what's right. Also he has a pretty blatant crush on Blake... at the moment, anyway.
Emerald, well, Emerald's an interesting mirror to him. Also disrespecting the law, also loyal to her friends, also conventionally attractive. The primary difference is her snarky personality and her deficiency in morality--traits that she probably picked up being a street rat. She is clearly aware of the concept, she sees the fall of Beacon as a sad event, but due to both her upbringing and her current company she has no actual motivation to do the "right" thing. Like Sun, she also has some form of attraction to a dark-haired woman. It's not quite as healthy as his crush, though...
Emerald and Sun were both, at one point, thieves by necessity. They both understand the hardship of having too little, they both understand the value of having companions, and they both understand what it's like to have the woman you are crushing on react negatively to your presence. Truthfully, Sun is the light to Emerald's dark, the dashing rogue to her cat burglar. They could easily see each other in each other, and that bond--plus a lot of hard work and effort--could lead to a relationship.
Of course Sun and Emerald have never met in person, so that would have to happen. They'd also have to shake off their respective crushes--I can see Sun doing that if Blake decides to pair up with somebody else, and Emerald might do so if Cinder... either goes too far or ends up lost on her own. Most likely this would happen after whatever mess is going to go down in Mistral, and even then it wouldn't be immediate--Emerald would still be very resentful of the events, probably imprisoned, and Sun would be quite mistrusting of her....
...but it would be just like Sun to reach out and try to understand why Emerald is "evil", and also like him to try to help her understand what morality is. And Emerald, who has never met anyone who both understood her and cared about her (at least that we know of), would probably react positively to this attention, if very slowly. A lot of snark and a few years of opening up later, and it might just happen that Sun Wukong and Emerald Sustrai form a Thieves' Company.
Masterweaver leaned back as the clipper growled to life, wiping his hood clean of grease. "Aye, there's a wondarrrrrrful sound, me lads! A ship ready and rearin' ta go, savvy? Now then."
With a twirl of his wrench, he turned to the other vessel. "This moit be a tooch hardarrrrr fer me ta rig oop, boot if thar's one thing bein' a pirate has taught me it's that tha hard things? They be worth doin'!"
Ozpin and Cinder, Cinder and Ozpin. What can we say about these two?
Ozpin is... a tricky sort to get a handle on. He runs a school and obviously cares for the students, wanting to help them grow... but he also runs a conspiracy to keep the greater evils hidden. His methods are the sort that only work if he's in the background, if he's distant; he can be the old wise mentor or the secret chessmaster, but only if he acts with a light touch. That said, when push comes to shove he will take action, and take command efficiently. There's very little personal information on Ozpin, so we're left with a man who wants to save the world but doesn't want the world knowing it needed to be saved.
Cinder is... also tricky, for much the same reasons. She wants to be strong, feared, powerful... but why? Why is she so willingly working with the bad guys, why is she so ready to cause Beacon's fall? Even factoring in season 4 information, we still know very little about her personally; all we know is she has a goal, she has manipulative methods, and she keeps a tight grip on her minion's actions. Cinder is tricky and adaptable, sabotaging her opponents and using her resources with precision and cunning that has earned her the ranks of true respect; every failure was merely a setback, and not even a big one at that.
Ozpin and Cinder both play a long, shadowed game, moving people around like pawns, taking exactly the action they need. Their desires are opposite: Ozpin wants others to be strong, Cinder want their strength for herself. Ozpin wants to be respected and loved, Cinder wants to be respected and feared. Ozpin has power, which comes with great responsibility; Cinder wants power for her own gain. We come again to a mirror of light and dark, and as opponents they'd respect each other quite a bit... but as lovers? That would take some time.
Because MisCon has specified V1-3 Ozpin and Cinder, we can say they both survived the battle of Beacon, though grievously wounded (this theoretical scenario has a shipfic being written between V3 and V4, so basically no Oscar or team WTCH). In the intervening weeks, months, years, the two of them continue to recover and duel each other through proxies, Cinder seeking to collect the power of all the maidens; sometimes she wins, sometimes she loses, but throughout their combat the two of them gain a deep respect for each other. Then Salem does... something, enough to earn Cinder's ire, so when she finally does gather the final Maiden's power she pulls a last minute turn of alignment, switching over to Ozpin's side to destroy Salem... before giving the man one final taunt of "catch me if you can!" and running away. It's not a perfect ship, but it might work, if done right.
"Whew!" Masterweaver leaned back as the engine sputtered to life. "Bit tricksy, this ol' heap is. Probably best ye brought an outdated one, ta be honest; Ozpin brand gears have gotten a bit beat up in their last batch, and the fire marbles from Cindarrrrrr productions all got cracks in 'em these days. Still, got this ol' beauty in motion... it'll probably last fer a raid or two."
He turned to MisCon. "Speakin' o' which, lad... ye want ta take these two out fer a test drive? I see a listin' ladybug oot thar, might be a good prey ta cut ye teeth on..."