CATS04 -- I hope you will be able to make it to your cruise -- its a great motivator
I'm sort of in the same boat - with the pre-existing conditions ... I may breakdown and by it for the cancellation provisions - since I am on the repo cruise and will be sailing during the peak hurricane season for both coasts
On that note -- I've been there & done that already. I sailed on the 9/4/04 (oops - Hurricane Frances 9/7/04 cruise). We were already down in Florida -since we flew down the week before to do WDW then board the ship. By Wedns. nite - we knew we were in trouble - and that just got worse. My nephew (I was traveling with friends & my sister) was in a serious car accident -- he didn't need to be hospitalized but had neck & back injuries. My sister was torn between trying to fly home on Thurs (all flights booked) and then they closed the airport at noon on Friday. We were stuck -- our brother -in -law practically stayed at our house and gave us updates on his condition. Thankfully he has made almost a full recovery from the accident.
By Thurs morning - POFQ - was able to release rooms to us to extend our stay -- we didn't have to change rooms even. We were going to stay by the Port for that Friday nite -- but that hotel was evacuated. WDW was extremely nice and gave us the same rate as the FL evacuees ($ 80.00 a night vs. $ 140.00). We ended up staying until Tues. morning .. but in terms of additional money out of pocket we only paid additional money for Sat. & Sun. nite (Friday was a wash since we would have been paying for a room by the port anyway).
DCL - comped all the passengers there room on Monday Nite. Food wise - POFQ food court was closed for 24 hrs during the storm (save money that way

). Picked up supplies at the supermarket on Thurs. nite before we returned the rental car $ 25.00. Extra food a disney I would estimate at $ 150 (Sat Morning, Sunday nite & Monday).
So -- the delay cost us $ 310. -- vs. the cost of insurance $ 200 (we are in our 40's.) Considering that we have sailed 3 times in Sept and only had a problem once -- we are ahead of the game (so far - knock on wood). Plus as many are aware DCL gave us shipboard credits, vouchers for our next cruise & a 50% refund.
Medically -- it's even more interesting -- since I didn't buy the insurance immediately all prior conditions are excluded. So... I called my health insurance carrier -- Oxford - Freedom Plan (option to go out of network if needed). After an interesting talk with a rep (and yes I am going to get it in writing before I leave) a trip to the Medical Facility is equal to an ER room visit at home ($ 50. co-pay) and yes they do pay for medical evacuation. So... my real concern is do you have to pay up front for the medical evac - or do they bill you .... I'm hoping I'll never have to find out but somehow I can't see any cruise line denying care (talk about a lawsuit) if you can't fork over $ 25,000 to be evacuated, and I can send the bill to the insurance to pay later.
Sorry for the extra long post --