Ahoy
I had a sailboat for about 5 yrs in Fla/Gulf Coast. I often found free anchorage where I could use my "dink" it get to the "hill". Mine was a shoal draft (shallow draw), so I was able to get in closer in many cases...depending on tide levels. Sometimes I could find "honey holes" (deep spots) just offshore or by barrier islands and even swim in with a drybag containing town clothes. (on the boat was most often nude...no tan lines, LOL).
I also found lots of places I could dock (with permission) for a few hours to shop, etc. Some bars in coastal areas have docks and will even bring drinks/food right to your boat. A word with the shift mgr and off I'd go for supplies. (often I could rent a bike from an employee for a few bucks, if any....tips and drinks go a long way). I've spent the night tied to many of those docks....mostly NOT alone *wink wink* :angel:
Like an RV, there are dump (actually vac pumps) that suck waste tanks on city and some private docks and marinas for a small fee...fill fresh water tanks too
I ported out of Apalachicola, Fla (best oysters in the world, yum). I had a deal with the dock owner and did a few maintenance things for slip rent. I paid about $7-10/mo for shore power to run my battery charger.
I replaced a dock board once in a while and go along and bang in loose nails sometimes. (a friend looked out when I was gone). One year I ran all new city water lines (PVC) under the dock with connections at each slip. ("Dink" made a perfect work platform). Anyhoo, that got me in good graces for quite a while around there.
I haven't done any boating in SD since '65, so I have no idea how things are there now. I suggest you make an effort to meet up with a few boatdwellers and ask some questions. They might have some "hidy holes" that the landlubbers have no clue about. (not all are willing to share, but a few beers go a long way sometimes).
Working while traveling the coast...I wasn't looking for work, but sail boaters sorta stick together and info floats around waterfront bars. Being in the Deep South (hail Dixie), I had many offers to work on Antebellum homes, which is my craft. (accepted 1 that was mostly lathework and some detail chisel reproductions of gingerbread of the era) I also had space on "the hill" in Apalach where I did restoration on old stained glass panels when I wanted to hang around for a while.
Ok, I'm prolly boring the crap out of everyone about now, so I'll just say that I really enjoyed that time in my life and would do it again, BUT....I'm the type that does something faithfully while I'm doing it for a few years, then I move on to something else. I feel I've been fairly successful in my travels and staying afloat financially (barely) and I wouldn't trade my adventures for anything.
I'm open to any questions and will be as upfront as possible. There are many boating sites out there, but I haven't found any that aren't all snooty about their hole in the water.
So, in the spirit in which Bob began this site I'm pleased to do what I can for this mobile way of life.