Travel Insurance

We struggled with that too. My determining factor was, what would I lose money on if we got sick and had to go home early? I always book hotel rooms as "cancel at least 24 hours before check-in for free" so I generally include just one night of hotel. If you are ok with carrying an airline credit, you could conceivably not include your flights. (For us, that was too much money to not get a refund, so I included airfare.) I definitely included cost of pre-purchased event tickets, etc. Insurance is expensive but losing money on the unexpected is also costly. I'm interested to see what others say about this, too.

I use Travel Guard and include all expenses I pay for in advance that aren't refundable. My initial policy is based on only the amount of money I have spent at that time (this time it was our RS deposit and airline tickets). As I pay more for things, I modify my policy online. I always buy/modify my insurance as soon as I have another expense, so I have "pre-existing conditions" coverage.

If you are ok with carrying an airline credit, you could conceivably not include your flights.

If the pre-existing conditions waiver is important then most travel insurance policies require all non-refundable expenses to be covered in order to receive the waiver.

If you want coverage for pre-existing conditions, you must buy the insurance within a specified time (usually 14-21 days) of the FIRST payment toward a non-refundable expense——usually a tour deposit. Expenses you include at that time would be the full cost of the tour, which you know in advance. If you later add more expenses—-flight cost, train tix, non-refundable hotels, etc., that does not affect the pre-existing conditions waiver if you booked the insurance within the window.

As for flight expenses, if you book a ticket that can be canceled for a voucher for future travel, that may or may not be considered a “non-refundable” expense and may not be reimbursed by the insurance if you have to cancel. Ask about that.

If you are spending 11 extra nights, just book a refundable rate and you don’t have to add it. But if you are tempted by the cheaper “no cancellation, no refund” rate, then you should add it later if you want it covered.

Regarding your pre and post tour hotels- I do really like Booking.com, but also always send a message about arrival time/confirmation to the hotel through the site once it's booked to 1) see how quickly (and if!) they respond and 2) if they did receive the booking information.
Per some other responses, if you choose cancelable up to 24 hours prior and also payment upon arrival, I look at that as baked -in " trip insurance" despite it inevitably adding more to the room rate. I just did this for a Berlin hotel, and it was $200 more for the week than the cheapest non refundable price.
So you could try it both ways and see how close they are, using the calculator tool usually provided.
I tend to worry more about the potential for additional medical coverage, depending on where I'm going. For Greenland the tour operator actually required proof of a very hefty amount, but traveling to a European city I chose a very basic amount.
I hope this was helpful! And that you never need to use it after purchase!

If you buy insurance with Travel Guard and modify the policy online be aware that even though you enter your credit card number when you submit the modification your credit card payment and therefore the trip modifications will not be processed unless you respond to an email that they send. If you call them and tell them your modifications then you will provide your credit card number during the call and the payment and therefore the modifications will be processed immediately.