Because I have over ten pages worth of notes here, I'm going to split my strategy up into sections as a day by day account would take too long. I used a combination of Traits, Lot traits, Club perks/boosts, Vampire powers, Reward traits and Mixology drinks, I also made sure my Sims were in the right Very Emotional state for whatever skill they were working on.
Set Up: I toggled through the Fortune, Family, Animal, Love and Vampire Aspirations and when building their house I knocked out a lot of whims to buy stuff, giving Delilah (Human) enough points to purchase Morning Sim and her husband Sylus Morning Sim and Speed Reader. They formed a Club, then I had them renew their wedding vows (I made them a married couple in CAS) and admire their new possessions (Both had the Materialistic trait) to get them in a very good mood. I bought them a Wishing Well and they both wished for skills. Sylus maxed out Mixology immediately, Delilah only got a four hour skill boost.
Vampire Powers: I set Sylus to work on the Vampire Lore skill as soon as possible, using Speed Reader, the Peace and Quiet lot trait and having him be very focused (Research Simpedia) while reading the books. He was done that evening so I took them both to the Narwhal Arms in Windenburg. By this time he had Bat Form, Occult Student (Maxed), Cause Hallucination and one or two ranks (I forgot which) in Child Of The Moon. He spent the night casting Cause Hallucination to rank up until he had enough points to max out Child Of The Moon. He also sparred with Lilith to complete a milestone and used to Dark Meditation to replenish energy. Delilah, in the meantime was painting on the easel outside the bar (Which is why I chose that place).
Clubs: I set the Club activities to whatever skill they were working on at the time, reading and Vampire powers, sometimes changing them depending on what they were doing at the time. I bought Rally the Troops asap, I also bought a skill boost for every level ten skill and the Focused vibe was purchased within the first couple of days. The Club was running all the time.
Rewards: Delilah's first skill was Painting so she could paint emotional paintings and knock out the Fortune and Painting milestones quickly. This way they both had Morning Sim and Night Owl by the end of the first day, they both got Savant not long after that, I wanted to get those rewards asap.
Lot Traits: I used all of the skill boosting lot traits, switching them when needed. Sylus worked on skills that could be boosted by lot traits during the day, but the ones that didn't have lot traits associated with them he did at night so they would get the Child Of The Moon boost instead.
Emotions: My Sims were always in the Very Emotional state needed for whatever skill they were doing, I used the following to help them get there. For overall happy boosts I made them admire possessions, decorations, woohoo, renew vows, reminisce, listen to music or donate to charity (Both had the Good trait). Rally the Troops helped keep their needs high, Woohoo was for fun and social and they washed their hands for hygiene. For other emotions I used Incense burners Cloud/Stargaze, Research on Computer, Emotional paintings and Club Vibes, Sylus dug up a MySims trophy to help his wife with the Playful Painting. I later switched to Emotion Potions when they purchased all the rewards I wanted them to have.
Festivals: I used these to my advantage, Geekcon was first so I had Sylus whip up some Sunlight Reversal Cocktails and Amygdelights, they both drank these before leaving. I quickly had Sylus Ponder Moves before he left, when they arrived he started a Club Gathering, setting a Focused Vibe to overcome the Energized moodlet from the Vampire drink. By the time they left Delilah had level 6 in Rocket Science and Sylus had level 6 in Programming and a shiny new computer from winning the Hack-a-thon! Next week they went to the Humour and Hijinks festival, in a Club gathering of course, Delilah joined the Light Side and told jokes to raise Comedy while her husband drank the Dark tea and pranked everyone for Mischief gain. They both maxed their respective skills before the festival finished.
Other Stuff: I gave them two pets, a Dog named Wolf so Delilah could max the Pet Training skill (Which she did) and Cat named Goose to keep Wolf company, the pets had the automatic feeder and laser litter tray to save time. The Amygdelight drink was drunk regularly to help my Sims master the Rocket Science, Programming, Video Gaming and Logic skills faster. Delilah maxed all the Minor (Level 5) skills and a few level 10 ones, sadly she fell just short of maxing Flower Arranging, finishing at level 9.
I think that's everything ... I think, I had SO MUCH strategy for this challenge (Literally a different one for each skill) that I have probably left something out, but I hope not, lol. I'll post some statistics, detailing exactly what skills were done, traits they had etc in another post later tonight as this post is getting way too long and it's dinner time here. I hope you enjoy reading and I'll be back later.