My last journey to the USA I had purchased TI since Oz to USA was a QF redemption and USA to Oz was a VA redemption - Amex does not, for example, does not generally provide cover in such circumstances. (They will if travel is purchased using MR points.)
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I use bank issued cards (Amex/VISA or MC) Combos where all you need to activate is to:
* Have spent a set amount per person ($250 to $500 depending in the bank and card combo) travelling PRIOR to departure.
* Have a flight over
and back (Does not matter if paid, redeemed or even redeemed on different FF programs). I often redeem on different airlines either for the major flights there and back, and/or for local flights once away and sometimes through two different FF programs.
This is nice and simple...and way cheaper to activate than many cards which require considerable spend or where you have to be able to prove that points redeemed for tickets were from that cards past activity.
Note: A key part of travel insurance is the CANCELLATION coverage. So if using this approach make sure you activate your card's insurance as soon as you commit to any sizeable spend that is not 100% recoverable. I will normally pay the fuel fines of redeemed tickets with the card that will provide my insurance and this is often enough to activate by itself.
If you are paying for TI, buy the policy as soon as you spend any significant sum. It costs no more to do this. Many people mistakingly wait till not long before departure to take out TI and so are not covered if something happens to stop/alter their trip.
My wife once had a cycling accident and we had to cancel a 6 weeks trip to Europe. As it turned out cancelling the redeemed SQ flights was cheap (it is always cheap), but the Amex Insurance paid for that small cost, plus the much bigger costs of a cycling tour, an an adventure tour, various train trips and some accomodation where we would have otherwise have been out a tidy sum.
Is there anything you can share by way of caution for those of us that use it?
