I concur with everything princesscinderella says. The one type of insurance and I only bought this once (expensive European trip I was doing with my son) that will cover anything is "Cancel for Any Reason" insurance. It's typically an add on to comprehensive
travel insurance. You typically have to buy this right away (a certain number days after booking the first non-refundable charge), and just get 75% of your non-refundable expenses back if you cancel. This though is what I used for the European trip in case DS got a new job and could no longer have the time off, an older relative not going on the trip was ill and needed our help, etc. In this case I had purchased (expensive and a splurge for me -- premium economy open jaw airline tickets) that I would have wanted to be partially reimbursed for if we couldn't go so we could go again at another time (like the following year).
Squaremouth and
Insure my trip are great sites and have good agents who can help you with one time policies too. I did research on my own first and then talked to one of these knowledgeable agents before I bought my policy for this trip.
To Orlando for me (it's usually more of a budget trip for me with most stuff refundable) but not fully on an offsite condo, I self insure. I fly Southwest though, so ticket vouchers or points never expire and can be used at another time. Disney tickets used could be used at another time (just pay increased cost if any). Rental car is fully refundable. If not staying at a condo, I get a refundable hotel (minimal risk of losing money).
If I care about medical insurance for comprehensive insurance I like Nationwide as they do higher limits than most other places and if I just need medical insurance I like GeoBlue. For our trip to Puerto Vallarta in February, I am self insuring except for the medical where I bought GeoBlue coverage. I know you didn't ask about that, but that is the insurance that is always my biggest concern. In the US we are all covered, but some in our party are not covered as well in foreign countries. With Orlando being in the US, that is never a concern for me on a trip there.