I got back recently from another ride from Miami to Key West over three days. The trail was mostly in decent shape, but there were stretches from Upper Matecumbe Key to Duck Key where the trail was blocked off because it was torn up from the hurricanes. Also near the deer refuge on Big Pine Key. There were also parts where there was obvious debris on the trail - dirt, small twigs/branches, and sand. There was one part just north of Duck Key where the sand was fairly deep in parts and could be treacherous if you hit it at high speed, but mostly it was just annoying.
Something to note for first time riders down there: the trail is meandering, sometimes not of great quality (from branches growing underneath, etc.), and jumps from one side of the highway to the other (a lot). If you're not in a hurry, then the trail definitely feels safer because you're so far from the traffic. On the other hand, the shoulders are often generous, straight, and smooth. If you're less concerned about being near traffic, then you'll definitely make better time on the road. Maybe this is an obvious statement, but it's something to keep in mind. Most of it is not a super-smooth, easy, fast trail like others in the U.S.
I didn't find a better way down to Key Largo, and ended up taking the busway trail again, and Card Sound Road. A nice rear-view mirror was helpful for Card Sound Road, because there were no shoulders to ride on. Fortunately, this time I didn't pick up any glass on the busway trail. If anyone has biked to Key Largo using US-1, I'd be interested in your thoughts about it. From what I've read, the shoulders aren't that wide, the road is busy, and the cars are flying by.
Leaving Miami early in the morning made a huge difference, heat-wise, for the 70+ miles down to Key Largo. I got to Alabama Jack's for lunch around noon and stayed until about 2:45 just to stay out of the midday heat. I'm not sure what others do to manage the 85+ days in the tropics, but for me the heat was really draining my energy. After about 11am I had to stop about every 30 minutes just to douse myself with water. I carried one bottle for drinking and one, sometimes two, just for pouring over my head and soaking my shirt. (And for perspective, I ride almost every day at home, so I'm no stranger to the saddle.)
Following up on the question above about what to do in the event of a "massive fail", once again I was offered a ride when it looked like I was in trouble on the side of the road in the lower keys. Last time, a lady with a pickup truck offered me a ride when I was waiting out a passing rain shower. This time, I was fixing a flat on the side of the road (my only flat of the trip - some stiff wire that put a tiny hole in the tube), and an even older lady pulled over this time to see if I was okay. Super friendly people down there.
I picked up a modest tailwind south/west of Marathon on and off all the way down to Key West this time.
Also, the snorkeling at Sombrero Reef was fantastic. There was a good excursion from Captain Pip's in Marathon - I made it down there on day two from Key Largo in enough time to catch the 1pm tour out. Highly recommended.
Baby's Coffee in the lower keys was a nice stop. They're bicycle friendly and the coffee is excellent. Not a lot of space to hang out inside, but when you're in there the A/C is excellent. :-) I also had some good fish tacos at Snapper's in Key Largo. I'd go there again.