Free-form betting typically has rather high transaction costs. Formulating a bet in such a way that all participants will agree on the mere proposition itself is time consuming for at least one party and also often demands substantial coordination from both or all of them. Sometimes it also requires attention from an independent arbitrator. Disputes over resolutions of bets can cause vastly more loss of value from all participants than any possible undisputed outcome would have.
Furthermore, as soon as you bet nontrivial amounts of money, incentives start to favour some form of shenanigans on the part of those offering the bet: concealing technical loopholes in the statement or resolution criteria, misleading other participants about what the proposition actually is, or being able to affect the outcome in some hidden way. Protecting against any or all of these is not trivial.
My opinion is that in short, trivial bets aren’t worth the time (except for purposes of practice in probability), and nontrivial bets are risky for reasons far beyond the question that is putatively in doubt. I would mostly leave it to risk-seekers and scammers.
Free-form betting typically has rather high transaction costs. Formulating a bet in such a way that all participants will agree on the mere proposition itself is time consuming for at least one party and also often demands substantial coordination from both or all of them. Sometimes it also requires attention from an independent arbitrator. Disputes over resolutions of bets can cause vastly more loss of value from all participants than any possible undisputed outcome would have.
Furthermore, as soon as you bet nontrivial amounts of money, incentives start to favour some form of shenanigans on the part of those offering the bet: concealing technical loopholes in the statement or resolution criteria, misleading other participants about what the proposition actually is, or being able to affect the outcome in some hidden way. Protecting against any or all of these is not trivial.
My opinion is that in short, trivial bets aren’t worth the time (except for purposes of practice in probability), and nontrivial bets are risky for reasons far beyond the question that is putatively in doubt. I would mostly leave it to risk-seekers and scammers.