Interesting, now that I think of it, I have never met someone (except pg) who is a painter and programmer. I've met several programmers who are writers, musicians, carpenters, etc, but never painters.
I draw cartoons/caricatures (examples here: http://www.smileecards.com) and have painted a few times, but I don't quite call myself a painter.
About teachers, I totally agree that good teachers earn the respect of the students by having high standard, calling students out on bad quality work. I once suspected a teacher only read the beginning and the end of essays, so I submitted a 4 page essay that contained a recipe for banana cake in the second and third pages; I received a B+!
This is a side project my partner and I worked on. We built it on Google App Engine. I made all the drawings using Autodesk Sketchbook Pro on the iPad.
Here is my general take on this:
Going to a top school can probably be a great experience, have you learn things from top professors/researchers in the field, get exposure to great companies recruiting at the university, be part of a pool of highly competitive high achieving students, etc. All this is probably worth a lot and might lead to one being better prepared, having connection or access to a network of people who might have more influence, connections, means, etc.
However, there is not sure path to success and the things mentioned above might give one a higher chance at success, but no guarantee. I would say that ones personality, ambition, and hard work play a huge factor in ones success, perhaps even a bigger factor, so I believe someone can be successful irrespective of the school they attended.
Taking on $100K+ debt at such young age is a huge risk as well. There are many problems with debt, but the major one I consider is how it ties you down and prevents you from taking risks and being able to take risks at a young age is really important. If one graduates with lots of debt, one has to have a steady job (and hopefully one that pays very well) to meet the financial obligations. That might hinder one's ability to take a job at an early stage startup or other opportunities that might enable one to learn and grow faster than working at a more stable company.
I personally like experiencing freedom from debt (as much as possible), so I would (and did) pursue the best educational option that would only cost an amount that I feel would still grant me a certain degree of freedom/risk-taking ability.
1) Prioritization: since there's never is enough time for one or one's team to do it all, figuring out what you can get the most bang for the buck (in your interpretation of ROI) is critical.
2) Keeping ideas alive: because of prioritization, sometimes one can't put much effort behind and idea or project that has promise, but is lower on the priority list. Keep feeding that idea/project, even if it means having another person or team carry it. Some great results have come from some things I couldn't commit to myself, but others were able to.
3) Balance: the startup mindset can lead to a lot of creativity and productivity. But try to keep a good balance with your personal life (whatever a good balance means for you: 80-20, 50-50, etc).
4) Itch persists: it's so true, after one's created something, and that something has reached an operational stage, being a creative person, the itch to create something else will become stronger with time until you can't resist it. Being unable to act on the creative urge is highly frustrating.
Google and Apple benefit from the volume of sales of apps through their "app" stores. By supporting a standard (and helping it be a good one, not one that has many proprietary interpretations), they can help extend the reach of apps, reduce development cost/time of app developers, and possibly increasing the volume of apps that get sold through their stores.
All these things that YC-funded startups have going for them (screened teams and ideas, network, support, etc) probably create more demand for them from VCs, giving them better leverage than non-YC-funded ones.
http://www.smileecards.com/card/einstein-on-simplicity