Epilogue via Author's Notes
As requested, here is an epilogue of sorts. It's more my telling of the outcome then writing it in story form.
July rolls around and Elrik holds his formal press conference announcing his stepping down. Representatives (the fathers) from SwissMedia and the Ootori Ziabatsu are there together with Elrik displaying a united front, the best of both worlds. No one bats an eye when the sons, Soren and Akito, are named as managers. What goes unsaid is the fact that Kyoya himself is not only funds but also owns everything. This was at the request of Kyoya to not raise too many eyebrows so his father's company can still save face for the negotiations being broken off early.
Since everything worked out so well, Yoshio was forced to recognize the relationship between Kyoya and Anna - saving Kyoya from having to become arranged. The "public display" wasn't until after Elrik's announcement however. This was also to keep speculation at a minimum. However, Anna was full force PDA as soon as everyone was comfortable, and Kyoya relished it all.
For the first time, Kyoya felt completely free. He had prove to his father he was more worthy than Yuuichi to become the Ootori heir. However, as years passed with Anna, he realized he didn't want it as intensely as before. While his accomplishment with Elrik was a huge success, he saw the future that lay ahead of him. If him and Anna married, had kids - he would end up like Elrik. Loving from afar and always on the go. He wasn't sure he wanted that. He worked to hard to just get hisfather to accept the relationship that didn't want all that work to be for nothing - for Anna to end up marrying someone like her father. No, he wanted to be with her.
A nosy reporter did some investigating and did discover that it wasn't Yoshio who was running the show, but Kyoya. It caused quite an uproar in the medical and management community. It was all over magazines like Money, Fortune, Time, etc. Kyoya loved it as the publicity brought attention to the businesses managed by Soren and Akito. ("Any publicity is good publicity, especially when there's no damage control that needs to be done," Kyoya always says.)
It was also discovered that him and Anna had been together for quite some time and speculation rose over whether or not that influenced the negotiations. However, they were already done, so those conspiracies fell short as it was poking holes in something that already happened, happened well, and ended up successful. The stories more turned to the blossoming romance between two tycoon's children. That, and they were the poster children for well behaved rich kids. (Think the opposite of Paris Hilton and the Kardashians.) Anna didn't like the publicity but Kyoya enjoyed it as he thought of it as a game. It was similar to "if I do XXX will they take it as XXXX" - so tabloids and other social magazines would have very confusing headlines and stories...then they realized they were being messed with...but it sold magazines and it brought publicity to the business - which... Any publicity is good publicity, especially when there's no damage control...
Kyoya's new company was called K Ventures. As with all ventures, the business is providing money to pilot ideas and gather a return on investment when they took off, which they always did. There are very few people in the world that can make a living off of ventures ... simply supplying money for people who have brilliant ideas. They are actually quite obscure. Probably the most famous one is Richards Branson (Virgin mobile, airlines, etc) - except they're usually his own ideas and he manages...but it's the closest example I can come up with. So Kyoya is a genius investor - he makes millions and doesn't have to manage anything except his own money.
Kyoya's medical company is AllianceMedica - where Akito manages the planned-holistic retirement/nursing community and Soren manages the extended stay care. Of course, it grows in popularity and eventually gets accepted by almost all insurances. The extended stay is considered a clinic (not quite a hospital). The community is just like a typical planned suburban community that has a clinic in walking distance, so that was never really an issue. The "at home" care is considered hospice, and that's already accepted by insurance companies. The major thing, is that it becomes more accepted across all continents...the United States being the last to fully embrace due to it's independent nature.
Elrik eventually retires completely after 5 years, slowing his involvement each year.
The Near Future
Jeff finishes up studies in Stanford and ends up meeting someone about halfway through. Unlike his relationship with Angie, it wasn't on and off. They met as classmates, became friends, and started a relationship after graduating. He ends up moving to New York and takes a job on Wall Street, eventually moving into economic politics on the Hill (Capitol Hill, Washington DC). Him and his new girlfriend get engaged while in DC and decide to move to Europe so she can pursue her career as an Engineer. They have their first child, a boy, two years after moving to Europe.
Sun and Elrik retire 5 years after "stepping down." Like rich old men, they just go all over the world sight seeing: Fiji, Galapagos Islands, New Zealand, the Artic, etc. Sun becomes really good at photography and ends up blogging his travels (under a pen name) so Sun and Anna can keep tabs on them. The blog skyrockets into popularity and he is considered a touring expert and is even offered his own tv show in addition to being paid for his blog. (Mind you, no one realizes it's Sun and that he's already wealthy.) So, for shits and giggles he agrees. He's something like Samantha Brown from the Travel Channel. (Watch it, it's really great.)
Elrik just enjoys traveling around with Sun (tv or not), but pays for himself. They become quite proficient in many languages (not that they weren't already).
Eventually, Elrik and Sun meet ladies themselves (Sun meets someone while travel-blogging and Elrik meets someone through the show), although in their older age - it's more about the companionship. Sun gets married but Elrik remains unmarried although him and his lady basically live together.
Anna ends up working in the medical field as a nursing assistant, much to her father's dismay. He wanted her in management, but she wanted to be with the people. Kyoya, well he was an investor and completely and obnoxiously wealthy. Eventually he manages the growth of both the community and extended stay care. (Akito and Soren manages "the weeds" - Kyoya's more oversight, if that makes sense. Kind of like Kyoya's the President of the company and Akito and Soren are Directors of a business line.)
The Far Future
Anna and Kyoya do get married. Engagement isn't really a big deal in Japan. It's more of a western thing. But Anna eventually wants a ring. She is a girl after all. Kyoya consents and has one made because he can't stand the idea of buying retail, whether or not it's from Tiffany's or Cartier. Neil Lane (celebrity ring designer who now does cheap jewelry for the common folk - think Kay Jewelers -) who has been intrigued by Kyoya's success, requests to make the ring. (He knew they'd get engaged eventually.) He designs the ring R04511 - an oval diamond in platinum. (I tried googling it, but it's probably best to just go to Neil Lane's webpage and look for the model number. I think it's two right clicks and then somewhere in the middle.)
Anna wanted rose gold, but Kyoya thought it looked dirty, so he got platinum. LOL... he's Kyoya, he can do that.
So they married "late" compared to the rest of the Host Club. They were in their late 20s.
One year after they married, they became pregnant with their first child. A boy.
They waited until their son was fully potty trained and mostly independent before trying for a second child.
Anna was pregnant with twins. One died, so they had to remove it before it began killing the second twin. (This actually happened to a friend of mine, it was very sad and tragic.)
The second twin was absolutely healthy despite being born a few weeks early. Anna gave birth to a girl.
They kept the whole twin and twin dying thing just between them, per Anna's request. She didn't want to remember or talk about it anymore. Kyoya complied. Anna also didn't want to get pregnant again because this was just completely traumatic and Kyoya got a vasectomy.
Anna stops working and becomes a stay at home mom shortly after the birth of the little girl. The kids are freaking brilliant. The son takes on more of an affinity for art and music while the daughter is more like Kyoya, super ambitious and shrewd sense.
Kyoya...at around... 35 is recognized as equal (everyone's afraid to say "better than") his brothers...but the clincher is when an article comes out saying that he's surpassed his father (bwahahahaha). It's around this time when they move to Japan.
Anna hangs out with the Morinozukas a lot. I believe they have 4 kids? (Can't remember what the author wrote in the afterward) and are still super close with the Suos. Ageha (the twin's little sister) comes to play as well. So really, Kyoya's new house in Japan becomes like a daycare for all of his friends kids. Which makes his sister very happy that Kyoya didn't have to sacrifice love to accomplish his goal.
Much to Kyoya's chagrin, his son eventually marries Tamaki and Haruhi's daughter. The resulting children are completely wild because they are too smart for their own good and independent. They all end up with many grand kids which Kyoya likes taking them to work with him (in turns) to learn the business (much to Anna's dismay).
They grow old and die happily ever after.
Author's Final Note
I did a bad thing and wrote this during the day - when I should have other wise been doing more productive things... I noticed some mistakes (like I accidentally erased the name of Kyoya's company) that I wanted to fix.
This is - by far, the best fan fic I wrote...which probably isn't saying much since this is my 4th completed story hahaha.
It was fun reading it and I'm really sad it's over, but thank you to everyone that commented. It really means a lot.
I guess I'll work on finishing my other two stories.
Thanks again everyone, this has been a great experience. And I promise, last update ;)