I'm in a nearly identical situation equipment and location-wise. I have a Cal 2-27 with an Atomic 4, also on Rock Creek. I did a fair amount of sailing years ago in college and the decade after, but just bought my first boat this past April. As far as sailing, I'm more re-learning than learning, so in that respect we have different challenges.
However, with all that sailing as a youngster, I had done very little boat handling around the dock. So for the past couple months I've been focusing on picking up that new skill. And I can tell you that it will come with practice. The first thing I did was go out with a single able-bodied hand--no "passengers" or family gawkers looking to enjoy a day on the water--and just made several runs at the dock. My slip is very tricky to get into, but after a few tries I started to get a real feel for how she felt while turning, slowing, backing, etc. I actually drew a diagram of my slip and posted it above my desk so I could engage in zen-practice during the week. I thought very carefully about how to get the lines
ready and where to tie the fenders
. I learned how to use the prop walk (to port while backing, to starboard going forward) to my advantage. I learned how to come to a stop before I hit the dock, and get that first critical line
tied up. My crewmate handled a fender
and boat hook, and offered some good advice about how to get in. Now I've got a set pattern that I do every time.
Getting some training is a good idea, I suppose, (never done it so I can't advise,) but in the mean time you might want to consider working on your BOAT HANDLING before you worry too much about SAILING. Take the boat out in the creek, and leave the sail cover on. Make a bunch of runs at your slip, with fenders
ready. If it doesn't look right, turn away and reset for another pass.
There is some hidden logic here: I sense a hesitancy that I have experienced in both boats and planes (another hobby from my past.) You are worried about either damaging your boat, or damaging somebody else's boat, or just looking foolish. You need to get over that before you can be comfortable in your boat, and you can't handle her well until you are comfortable.
I'm very far from an expert, but I'd be happy to come by and take a look at your slip situation, to see if any of my recent learning would be of help to you.