Long flight plan

I'm planning to fly from Boston to Key West next month
with a stop near Bethesda on the way down and in Charlotte on
the way back. I'll need/want to make some additional stops along
the way, of course. This is a longer flight than I have made before
and much of it will be through states I have not flown in before.
So, I have a bunch of questions:

1) What do people like to use for flight planning for something
like this? Laying multiple sectionals on the floor next to each
other seems a bit painful. Is Aeroplanner a good choice? If so,
is the basic Aeroplanner the right level for this kind of thing?

2) I'm thinking of flying to Tipton (FME) to get near Bethesda.
Anyone have opinions on this airport? GAI seems to have gotten
a lot of negative comments on AirNav, though if the weather is
bad I'll probably go there instead. (I miss being able to fly
into College Park!)

3) If I fly into the Washington ADIZ IFR, can I cancel in the air
when I have the airport, or do I need to cancel on the ground? How
does switching over to the CTAF work if I'm supposed to be maintaining
communications with ATC while in the ADIZ?

4) I'm thinking about stopping at North Myrtle Beach (CRE) for
a fuel stop in at least one direction (nice comments on AirNav).
Anyone else have comments?

5) Is there an airport about 300 miles north of Key West that
would make a good place to stop for fuel/food? (I'm trying to
keep legs to about 300 nm each so that I'm only flying about 2 hours
before stopping, since my wife won't tolerate being in the plane
much longer than that -- plane cruises at about 155 knots).

Any additional comments/suggestions will be appreciated!

-- David

--
David Rind