Economically speaking I tend to find it a bad idea. Not fiscal economics, but emotional economics. There are several possible outcomes that have to be examined.
Bet for your team (Favored):
Team Wins and Covers - Maximum Happiness
Team Wins and Misses Cover - Happy about win, upset over lost money.
Bet for your team (Underdog):
Team Wins - Maximum Happiness
Team loses and Covers - Upset about loss, happy over won money
Bet against your team (Favored):
Team Wins and Misses Cover - Happy about win, happy over won money, upset about having to pick moments where you rooted against your team to score
Team Wins and Covers - Happy about win, upset over lost money
Team Loses - Upset over loss, happy about won money
Bet against your team (Underdog):
Team Wins - Happy about win, upset over lost money
Team Loses and Covers - Upset over loss, upset over lost money
Team Loses and Misses Cover - Upset over loss, happy about won money, upset about having to pick moments where you rooted against your team
So out of 10 possible outcomes, only 2 of them will help you to achieve maximum happiness and they can ONLY occur when you bet on your team.