First of all Welcome to Cruisers Forum!!!
As for your docking
question it is going to depend on the slip mostly. Picking a marina that is protected from the wind
will go a long way to making your job easier. Also consider a mooring
instead of a slip, if you overrun it, the ball hits the hull
and thats about it.
I personally do not like to single
hand a sailboat. Have done it in the past and will probably do it again, but only when I have too. For me its a safety
thing. One wrong move and your unconscious in the water
. If someone else is on board you at least have a chance.
Since the boat will be new to you there will likely be equipment
failures. Having another person on board that can manage the boat while you fix/figure the problem out can be quiet handy.
Without a lot of recent sailing experience it probably would not be wise to set such a lofty short term goal. Why not enjoy some company with friends (even if the do not know how to sail) for the first few years and then see how it goes? You could also check out the local racing
circuit and see who is looking for crew. That way you could see how others handle larger boats and sharpen up your sailing skills. Someone is always looking for a grinder/rail meat.