From an economics viewpoint (expected utility theory), the prescribed way to approach a series of bets is to focus on expected utility (for example. wealth). This leads invariably to Kelly staking and maximizing the long-term expected growth rate of one's bankroll. With this approach, the handicapper is advised to play every race where he has an edge (namely, "bet your beliefs"). By contrast, from a psychology viewpoint (prospect theory), the prescribed way to approach a series of bets is to focus on loss aversion (pain of losses far outweighs joy of wins). This leads invariably to session handicapping and minimizing regret.
If for example, we define session handicapping as a day's wagering, then it is possible to adapt Belgian mathematician Thomas Bruss’s Odds Algorithm (http://www.ems-ph.org/journals/newsletter/pdf/2006-12-62.pdf) to determine when is the optimal time to stop betting to enhance the probability of ending the day in profit. In other words, the odds algorithm works out after which race during a day's session you should quit assuming you are ahead!