We've done the AICW several times in our Santorin, going outside when favorable but having been inside for the entire route from southern Florida to Norfolk at one time or another.
There are no bridge issues. There are many depth issues.
The "holy grail" is "Bob423" - google him if you do it and get his routes, which are foolproof and he identifies those sections that absolutely need to be timed with the tide. The charts are not accurate and you can go hard aground smack-dab on the "magenta" channel line of your charts. Follow Bob423, where sometimes you must go outside of the channel markers. You can even do the Dismal Swamp route but you will regularly bounce on submerged stumps - we will not do that again.
That being said, the ICW is an excellent way to proceed when you do not have a "weather window" to go offshore, or if you simply want to slow down and "smell the coffee" where there are many very appealing places to explore and relax. Several stretches also offer great sailing in calm water when the wind is right - we've run whole days sailing at 7-8 knots.
Craig Briggs - s/v Sangaris / SN68 Tropic Isle Harbor, FL