Travel insurance for +65, 'medical conditions'

Yes! unless you have say an annual policy, in which case any new condition needs to be declared, and is in essence may be ‘pre-existing’ before you depart on your next trip. For annual policies you may need to seek reapproval if a new condition crops up.
But as I said, I found covers where this does not apply. Even in annual. What you are saying is that if you buy annual cover, then develop a condition prior to the first booking in that cover means potentially not covered. Never covered in fact.

Cover more does cover you for new illnesses even for annual as follows:

The key is when each trip was booked in relation to when the new illness developed.
For example, if you purchase annual insurance in January:
Trip 1, booked before January: A genuinely new illness diagnosed in March may be covered, subject to the policy conditions (eg not pre existing)
Trip 2, also booked before January: Potentially covered too.
Trip 3, booked in April after the March diagnosis: The illness is now a pre-existing condition and may require assessment.
So it isn't necessarily only the first trip.

It confirms that for annual policies, the Relevant Time is calculated separately for each trip: when the policy was issued or when that particular trip was first paid for, whichever is later.
 
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