Only remotely related to your question: When I was studying poker, the common wisdom I read everywhere was to never play without real money being involved. The justification for that was that people behave completely differently when no real money is involved, and so skill in play-money games does not translate at all to real poker. Apparently even stakes as low as $0.02 (translating to maximum loss for an entire game being about $5) make a difference.
I think the regulator issues could be easily overcome with bitcoin and TOR. I would be actually surprised if there was no betting exchange or sports betting site there, and those typically allow you to also bet on some non-sports events (elections, etc.).
Only remotely related to your question: When I was studying poker, the common wisdom I read everywhere was to never play without real money being involved. The justification for that was that people behave completely differently when no real money is involved, and so skill in play-money games does not translate at all to real poker. Apparently even stakes as low as $0.02 (translating to maximum loss for an entire game being about $5) make a difference.
I think the regulator issues could be easily overcome with bitcoin and TOR. I would be actually surprised if there was no betting exchange or sports betting site there, and those typically allow you to also bet on some non-sports events (elections, etc.).