Nathan, what a wonderful journey into the future. Your three points are interesting, but I think pt 2, working with machines is probably the least you will have to worry about teaching. Children born into a high tech environment adapt very quickly to their world. Although said somewhat facetiously, if you have problems with your IPAD, give it to your kid to fix. I recall when computers first came into wide dissemination and my big sister having a difficult time with a new application, when my little niece (a second grader) asked her mom what she was trying to do…she listened and said, oh…you mean this? wham bam, it was done…and off my niece went to watch TV…no big thing. (My sis by the way has a doctorate and also a nursing degree (with a masters in some sort of blood thing). Considering the tech base that would have to be already emplaced, I think we can forecast further evolution in capability, but having to learn working with it? probably not an area that will require a lot of resources or attention.
As for pt 3, mankind will have to protect its humanity. You point out very salient points on preserving history and art, acknowledging that we will also be transporting our full humanity of virtures and vices. Bluntly, the only population you will be able to screen for and select virtues, mitigate vices, and encourage/select skills and abilities with anything like accuracy will be the first colonists, after that, the next generation will be uncontrolled. Within a few generations, while you may have a higher base line IQ, the human population will have spread back across the spectrum, with personal drive/ambition/scholarly pursuits/dedication to the original mission no longer in a tight cluster of common focus, it will be spread out around the entire X/Y axis…and you will have humans that want to pursue vocational type endeavors to the exclusion of acadmics or vice versa. Some will have no desire to see beyond the walls of the colony, nor any desire to push those walls any further. While others will want to leave and see beyond the horizon.