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Broadband, mobile, energy, insurance, money and software.
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BEFORE YOU BUY
With broadband, mobile and insurance, the contract matters far more than the first month's price. Before I sign up, I check the total cost over the whole contract, what happens to the price when it ends, and any mid-contract price rises.
Comparison sites are a good place to start, but check the provider's own site too: some deals are only offered direct. If you're out of contract, ask your current provider to match the best price you've found. They often will.
For software and web services, see if there's a free trial or a cheaper annual plan, and set a reminder before it renews.
QUICK ANSWERS
Read the contract for annual price rises before you sign, and check what you'll pay when it ends. Switching or renegotiating at the end of a contract is usually the biggest saving.
Often, yes. If you're out of contract and have found a cheaper deal, ask your provider to match it. Many will offer a better price to keep you.