Hi
hope I can help!
First, I've heard of some people getting some Vallium or something similar from their doctors for flying. You're not the only one, so I'm sure your doctor would be able to suggest something.
Then, try to fly into MCO, there's also Sanford International in Orlando, but you can't get Magical Express from there. Magical Express is a luggage service as well as a transportation service to and from the airport, so long as you stay on property, it's free. I've used it before, very simple! Very convienent!
I would recommend Pop Century sans car. It's the only value that doesn't share busses--in other words, they have dedicated service. I've stayed at Pop and All Star Music, the theming of the value resorts is really neat, and especially if you're going by yourself, it's definitely do-able for a few days. With a family of four, the rooms seem to be small, but when I went to both I was with one other person and had plenty of space.
If you're thinking of the Premier Pass, the advantage for you would be that you'd have access to the resort discounts at WDW, usually it's somewhere around 30-40% off values! If not, the values comparitively cheap, so I'd definitely do a break-even to see which would work better. Remember that at WDW you have 2 choices for your 7 day pass (if that's the route you want to go!) You have the Magic Your Way (MYW) pass that allows one day/one park admission for each of those 7 days or you have the Parkhopper option, which allows you to go to and from any park during the 7 days. The nice thing about it, is that you don't have to decide on the parkhopper option until you're there. It's about $50 more for any ticket, so my suggestion is to get the 7 day one day/one park pass and decide once you're down there if you'll need the parkhopper. If you don't, you've just saved yourself $50! There's also the non-expiration option, but honestly, it's not worth it unless you know when you'll be heading back...the regular tickets expire 14 days from first use, check out
www.undercovertourist.com for cheapie tickets.
I've gone to the parks and done strictly counter service and had a great time, so if you're keeping budget in mind, don't feel like you have to do a sit down meal every day. You certainly won't be eating burgers & fries every day! (I've done 2 Dining Reports on the Quick Service DP, links are in my signature.) You don't really need to do a dining plan, as a solo person, I don't think it would be worth it, IMHO. I think it's a better deal to book everything separate if you have the time.
That's a brief overview, please don't hesitate if you have more questions! I'd be happy to answer them