I never have for Orlando, but for me I usually am flying Southwest, so can if I cancel flights use the travel funds for something else. We live in the US, so our medical insurance covers us in Orlando. Unused tickets can be used on another day and applied in the case of Disney to another year with just paying the difference. The one thing that I would usually be out on a Disney trip might be a condo rental from an owner (maybe 1K or something like that), but that's a low enough amount for me that I can self insure. And sometimes for shorter trips all I have for lodging is a hotel that is fully refundable. I have not had to cancel a trip that I have booked yet and have been coming to the parks since 1971, but "knock on wood" with that comment. We always stay offsite.
I buy travel insurance for cruises and for international travel. The main thing I am always concerned about is medical insurance and med evac insurance. That's the part that I can't just self insure, too much of a financial risk. If I am just buying medical and medical evac, I often go with GeoBlue. At least pre-pandemic it was good coverage and really inexpensive if you're young, but could be cost prohibitive from then if you are older. For comprehensive travel insurance (If I want that), I usually go thru a broker from a site like insure my trip, after I have an idea of what I want. (If you are looking to be able to cancel a trip for any reason, you would need a cancel for any reason policy and these are pretty pricy and maybe refund you something like 60-75% of your costs if you decide not to go). I am considering this when we eventually do the trip we were planning to Paris and Belfast in 2020 that was canceled, something more like a "once in a lifetime trip" with larger expenses than I would want to self insure for (e.g. super expensive non-refundable airline tickets, etc.) We aren't trying this in 2021 or 2022 (have to see borders open, some herd immunity, etc.). We are just sticking to the good ole' USA for 2021 and 2022. Have to see how things look in 2022 and maybe?? I'll rebook this for 2023 (cautiously optimistic). I just don't have the heart to book any travel that I don't think I have at least a 95% chance of going.