TSA: the usual bans on wierd electronics, gels, liquids and stuff can be waived so that a person can bring meds, devices etc. with them. You can read the TSA info here.
Service dogs: Many people have written about travel with service dogs recording various challenges, you can read another point of view here. TSA and airlines will allow service animals in the cockpit of the plane. TSA requires service animals to be visually identified. Although the federal laws regulating service animals currently prohibit discrimination such as requiring a license, many counties and states do have separate tags for service dogs. Ours has a county tag and we are carrying an affidavit from our doctor, just in case. We informed the airline when making our reservation and they were very helpful at least over the phone. We'll see how things are at the airport!
Wheel chairs: We are gate checking ours and getting a lift into the plane seating. Gate checking makes me nervous, they better not lose it!! Also, we have to change planes, so they are meeting us with a cart and assisting with transfers.
Meds: we have all kinds of meds, liquids, solids and gels. Also, over our luggage allowance. The airline is not charging extra for her extra bags and TSA assures us that although it will take longer to screen us, that simply declaring our stuff at the screening point will keep us out of trouble. Everything should be allowed through.
Rental cars: We will rent a van-- this time we don't need a ramp, but we did find this disability van rental service.
Easter Seals has a great website on accessible travel in many locations, including public transit, hotels, rental cars, airport etc. Check it out!
Of course, that is all planning and if I know anything about travel it is that nothing goes as planned. I'll report back afterwards with a retrospective! Wish us luck!