Fortunately, there are no inspectors to deal with. Property is in the country and no permits, inspections, etc. are required. I just want to do it right. I have decided, unless advised otherwise the day of installation, that I will put in a pull box and break it down into two sections. Use 2" pvc, connected at the main panel (not wiring); plenty of wire lube, and a total of 4 other helpers lending a hand (including the electrician).
If...I can straighten this out to 500 ft. or less by going through the woods, I will spend a day with the chain saw and brush hog clearing out 300 ft. or so through the woods wide enough for the trencher.
A couple of notes to others who offered advice and opinions: looked into solar, but decided against it since it was only going to save about $700 (net taking into account the 12V conversion for the hoist), and I would still need to run trail lights. Plus harder to guard against theft, since the boathouse is in a remote and secluded location out of sight of our house or even other property owners. And my cost will end up at around $2.10 per foot for the wire, elbows, pull box, and conduit.
I appreciate everyone's help, comments and advice on this one, because I truly am an amateur when it comes to wiring. It will happen one week from today, weather permitting.