"Selectquote" is a great place to start. They have all the rates and policies for different companies and can save you a dozen phonecalls. Very low-pressure salesmen.

Get term life insurance. Stay away from universal/whole life insurance... it's a huge waste of money, which is why the insurance salesmen push it so hard. More money out of your pocket and into theirs. They will make it look real good, but run away if they keep pushing it.

When to start? Depends. Do you have any kids to send to college if you were to die tomorrow?

How much? Also depends. How much to pay off the house so your widow won't get evicted while she's going back to school for that nursing degree? Don't get too much... you don't want your widow's new husband living in a mansion and buying toys (boats, RVs, flatscreens) with your insurance money. A good rule o'thumb is 5 years salary, but good luck figuring out how much that is for a regional pilot these days.

For the biggest savings, get a 30 or 40-year plan before you start flying. If you're already flying, Banner Life Ins. has some good rates and they're pilot-friendly.

Finally, shop around before you buy group insurance from your employer or ALPA. Could be a steal, could be a rip, so find out before you sign.

Good luck!