We have been to Jamaica six times and have never been questioned about medication even though we carry a copy of our prescription with us. Also have never been asked about amount of cash or funds we have except on Customs form which requires a declaration if over a certain amount (Believe the figure is USD10,000). Our flight from the UK is 10 hours but find a good book and ipod helps make the journey less boring.
We returned home last Sunday after another great vacation so just enjoy it.
My wife and I due to age and ailments need to take a lot of different tablets on holiday with us in our hand luggage. Customs job is to stop drug trafficking so as long as the tablets are still in there original foil wrapping it would be very easy for anyone who looked in your bags to see they are tablets for medication so you need not worry (and even if they were loose most security people will know what ecstasy, cocaine, heroin etc looks or smells like (if they have dogs) and if the improbable was to happen and you were arrested tests would soon prove they are not so don't worry). You could take a doctors note if you like but certainly in the UK they cost quite a lot of money (approx. £35, estimate about $55), you could just take your last prescription note with you as evidence (not sure if you have them in the US, but its the slip of paper the doctor gives you to take to the pharmacy with your items listed on them) so if they were interested in your tablets they can also see written evidence of what you are carrying. With regards sufficient funds, I have never heard holidaymakers ever being asked in any tourist destination worldwide but I would suspect it might possibly apply if you were planning on living/working in another country and not just spending two weeks there so don't worry and enjoy your vacation. With regards flight worries, just take a good book to read or watch the on-board movies, listen to music on your MP3/MP4 player and the time will pass or as some people do, have a couple (or 3) alcoholic drinks at the airport as I find that helps me sleep and makes the journey seem quicker.
By prescription they mean the info that is on bottle/pack from pharmacy. The sticker that has dr name, what pills are, dosage, etc. in other words you shouldn't put your pills in a ziploc bag, leave in original packaging. But all that being said, i travel frequently with scripts and have never been asked to show them to anyone.
By sufficient funds, they most likely means incase anything were to happen, you should have access to money if needed. For example, i wouldn't suggest going to another county without money or credit card. Just in case. I think majority of people bring some money and have credit or debit card.
Lastly, for plane anxiety. You may want to try something like dramamine that can help you sleep. I find most helpful to always have something to do. Read a good book or download shows/movies on my ipad to watch.
Wow thank you for all the reassuring responses! This has been immensely helpful! I also found a website to help with the flying anxiety http://www.flyingfear.net/ and it really helped calm my fears. I am officially prepared and completely excited to get to CSS - (incidentally, one of the many reasons I chose Sans Souci is that it means no worries). Our flight is from Philadelphia so it's only 4 hours from paradise! Thank you everyone!!