2) Re: skills - I do everything but program. And by everything I mean everything - funding, prod dev, marketing, sales, operations, strategy, etc.
Great point about not doing something driven by guilt. Thanks for your feedback.
At that point, maybe you can have a go at doing something along the lines of "Start Small, Stay Small":
http://www.amazon.com/gp/product/B003YH9MMI?ie=UTF8&tag=...
The idea being that with a niche product, it's not going to be an all-or-nothing venture, and you'll be able to run it just fine from wherever you are - no need to be somewhere where startups are 'hip' and you can recruit 30 people after you get your millions in funding.
don't just read, but write too
If you don't know who you are professionally, it's probably because your heart isn't in whatever it is you do. Quit feeling sorry for yourself and learn to program.
Awesome! You can start by reading 1 book a week, which is an aggressive but doable goal. To some it may not sound like much but if you have not been making a habit of reading regularly, it will take you a while to get back into it. In a year you will have read 52 books. I am of the belief that compound interest is most effective when you have staggering sums of money. It is second most effective when it comes to knowledge.
Amazon will sell you books for cheap, but there are many business classics that will probably be available at the local library. I bet your local library will at least have one of these seven books:
How to Win Friends and Influence People by Dale Carnegie
Think and Grow Rich by Napoleon Hill
Seven Habits of Highly Effective People by Stephen Covey
{anything} by Seth Godin
Positioning by Al Ries
Getting Things Done by David Allen
21 Laws of Leadership by John Maxwell
I'll repeat the advice out of one of Peter Drucker's books: the only way to really improve in life is to feed back from actions to results. Try to do something. When you fail (and you probably will, the first time), take an honest look at your performance, and identify one thing that you could've done better. Then do it again, but this time do that one thing differently. Did you get better results? If so, find something else you could've done better, and practice that next. If not, do it differently again, and measure the results. Repeat until you're doing everything awesomely. You have now mastered the skill.