Losing $5 and losing $100 are both bad but I know which one I'd pick. They are not equal and insisting they are is what led us here today.
The better solution is not to lose any money at all, and in the long term that's the goal. But in the mean time I'll pick $5 every time.
Realistically those are the only two options. Voting for Bernie Sanders or the NDP would not have changed a single thing and wishing won't make it so. And if enough people don't vote for the lesser evil you risk the worse one winning. That's how the world ended up with Trump.