Welcome aboard Jerry. You have picked a good boat for such an adventure and with only 3.3 feet of draft, you'll be able to get into places that most are denied.
As for Duke, you might start teaching him to use a "Potty Carpet" for doing his business. Essentially a square of AstroTurf with grommets in the corners that you can spread out and tie down on the foredeck. Aboard ship, the (relatively) solid waste is collected and disposed of through the head as usual. As for the "wet stuff", you can just fold the carpet up and dunk it over the side a few times. Rainwater (and you will endure rain) will rinse the salt out of it out adequately as will wash downs with fresh water when you stop for fuel.
As for anchorages, in addition to Active Captain
(registration required but free), there is also the Florida Sea Grant Anchorage Inventory
as to the southwest coast of Florida and the on-line guides available through the Salty Southeast Cruisers Net
which covers the entire Atlantic ICW up to Virginia and beyond.
As for your self steering, a self contained Tiller Pilot is an inexpensive and effective solution:
This and other similar units are available through the Sailnet store. (See Tiller Pilot
). Based upon my own experience I happen to favor Simrad but others will certainly advocate for Raynav and other makers as well.
While you are preparing for your trip, a good read that you might enjoy is "Princess" by Joe Richards. It's an old book that chronicles a trip just such as yours by a guy about your age but during the late 1930's to 60's. You'll have to find it used I'm afraid, but it's a great read and Joe was a wonderful painter.
N'any case, good luck with your voyage and please stay in touch, eh?