Sailing in an out of the harbor is the easy part. If you are heading out or in directly upwind, you need to be confident that you can nail you tacks. If you do blow the tack and wind up on the harbor mouth breakwater you need to know how to reverse the rudders and back wind the main to get off the breakwater, swimming or paddling around may be an option.
The hard part is getting on board and away from the dock and then landing back at the dock, securing a line on the dock and getting off the boat. You either have to do a balance beam walk down a hull from the dock to the tramp or bring the boat along side and take off. Returning to the dock presents even more problems. Somehow you have to turn directly into the wind and coast right to the dock so that your crew can secure a line on the dock. A Hobie goes dead in the water and starts going backward very quickly. You first attempt will almost certainly under shoot and you will have to get under way without hitting the dock and try again. If you do over shoot, you now have a ding to repair. Lowering the main and paddling is an option.
Don't forget that you have to raise and lower the main from the tramp. Departing and returning from a dock can be done and it can be done single handed. It is almost inevitable that you will ram the dock and get to brush up on ding repair as part of the learning process. Having somebody on the dock with a boat hook as a back up, if possible for initial landing attempts would be awfully good insurance.
Bob- great information, thanks for your input!