Overlapping Travel Insurance. What would you do?

Yes, you should be OK. We had an incident like this - we had to cancel a fully paid-up holiday and also a deposit paid on another one, because of my husband's cancer. The company paid up for both claims, even though the second holiday was scheduled to take place after the annual policy expired.

I have phone my insurers up and was told as long is there is no break in the insurance policies then I am covered. Just need to get the rest of the family covered now.

We have free travel insurance with two different bank accounts I can see no problem unless the insurance companies thought you had fraud in mind . Why not just take out insurance for the May holiday instead of a yearly one if it worries you ?

As Jalima says, have a word with your insurance company,they may do you a deal.
I tell my company everything, if you don’t you could be in trouble. I have always found them very helpful.

Phone them up, I’m sure that if you stay with the same company they will, but best to check.
If not then when you change Insurer, you will have to check that they will accept the previous booking and insure it.

If I don't, will the annual policy pay out for the 2019 holiday if something happens to me between now and October to prevent me travelling in 2019?
I think it should do, but in fact it would be better to phone the insurance company and check as they are notorious for wriggling out of paying out on the slightest pretext.

As for having two overlapping insurance policies, I have that as we have one through the bank which will not cover for medical conditions but would cover for lost baggage, delays etc and also take out another one which covers for specific medical conditions.

When DD had some equipment stolen when she was in Europe we put in a claim and half was paid out by her travel insurance and the other half paid out by our household insurance. The insurance companies seemed to sort that out between themselves.