> "But it hasn't resulted in the kinds of professional contacts I had hoped for."
I know this is off topic but... perhaps you'll have better success at exchanging information with fellow entrepreneurs at a local Meetup group (assuming you live to a nearby group)? http://www.meetup.com/
> "Often, financial problems are clues to something going wrong and also serve as a motivator to overcome your problems. I am not in the least concerned about stigma. I am concerned about removing valuable information from the system and making it radically more difficult to figure out what is going wrong, thereby making it harder to fix the problems because we are blind to them."
I see what you're getting at now. Three points:
1. The 'basic' part of basic income is important, as it's only meant to be enough money to cover a basic standard of living (i.e. food, shelter, etc...). If someone wants to have higher material wealth, they either have to earn it, or they have to learn how to stretch their basic income further. This process of stretching the basic income further relies on frugality and creativity, the same frugality and creativity you're suggesting only those at the top have. I'd suggest being poor can teach you those same lessons.
2. Money as a source of information isn't being lost. Again, the basic income covers the basics. Even if the market for bread and rice is stable, the market for luxury goods would be just as variable as before.
3. In your opinion, what is the purpose of money? In my opinion, the purpose of money is to facilitate trade. Trade can be seen as a form of collaboration. This collaboration relies on trust that what someone can produce has value. However, sometimes even when someone can produce something of value, they're blocked from doing so due to a shortage in tokens of exchange (money). For example, when the Great Depression started, you still had the same skills in the economy as before, but fewer means to coordinate the productive use of those skills. What I'm saying is that money has value as a means of exchange, but not as a means of production. If work is an engine, then money is the lubricant. You don't produce a more efficient engine by restricting the volume of lubricant to the smaller cogs.
> "Alcoholics often continue to drink if it isn't ruining them financially"
Alcoholics often continue to drink even if it is ruining them financially. Addiction isn't curbed by logic alone.