Welcome, fellow Eastern Shoreman. I'm out of state now but will be returning to the Kent Island area in a few years.
I pursued that same question some time back, but for newer models. I'm not familiar with the particulars of yours. I have to believe the issues are similar. My conclusion: the cleat arrangement is optimized for Pacific Northwest (PNW) marinas that are almost always floating docks, and side tie strategies with fenders pulled tight against full length finger piers.
That's great if that matches your conditions, but as you know floating docks are more the exception than the rule on the Bay. As best I can figure it, you just have to loop over cockpit rear sides, and snake it under the short rails above the cockpit rear, and through the swim platform rails. Exactly what path you take depends on the exact angles you are working with at your dock. Its far from optimal, but seems do-able. I say "seems" because I have not yet pulled the trigger on a boat and can't say for certain. It appears that often the seatbacks in the side cockpit seats are at risk of damage by the lines, but those can be popped on and off and stored in the cabin when not under way.
Once you solve this on yours, I'd be interested to hear about it.
And once you solve that, now try to solve it with a dingy hanging off the swim platform that creates no acceptable options for tie-up. In fairness to Ranger, to be clear, until you get up to boat sizes of approximately 40 ft and up with big cabin roof areas with crane davits, all boats have this dingy problem with solutions that range from bad to less bad.
