Actually access is not the issue. It is boat set up and ability to handle the boat under the circumstances. The latter equates to practice and lots more practice. The former is easy. First you do want a windlass, especially as you "age"--you speak of retirement and joint replacements. $600 for a windlass is a small price to pay for the ability to drop and retrieve the anchor at any time you want. Yes, if you are in rough water, you will want the anchor secured--but you can reach a securing line from the fore hatch, or even bring it back to a fitting which is along side the window by the helm.
The 22 allows you to easily reach the spring line cleat. You don't use the bow cleat in tying the boat to a dock--at least initially. you use the cleat by the window. Some boats don't have a cleat, so I put on a pad eye, and us that instead:
Here is a folding pad eye (rated at 4500 lbs), which is thru bolted into the side deck (as you see which is very narrow). The fender and a dock line are attatched to this pad eye. (folded down, it is not an obstruction as you go forward, holding onto the railings on the cabin top (more should be added than are standard).
As you dock, I have yet to find a situation where I cannot either pass a loop of line, toss a loop of line or secure to a cleat out of the window. If the conditions are calm, then you walk aft and secure a stern line. I try and approach starboard side too the dock, but you can reach across if necessary to the port side. If there is a condition pushing your off the dock, this line acts as a spring line, and the engine is left in gear, as you push the stern to the dock, with the prop, and then secure the stern line. You then have plenty of time to put on bow, spring and breast lines as necessary. I have used variations of this in boats up to 62 feet in length, when single handling and docking. The use of a spring line to hold the boat in position until the other lines is a very common "trick" of the trade. You will see it used even in megayachts and commercial vessles.
True there are any number of boats which have "bow doors"--but you give up a lot with that. Usually a forward bunk. The Nomad Nimble is an example of that--so is the "adventure craft". Excellent access, but you give up something.
As far as maneuvering--the C Dory is one of the easiest boats to manuever I have come across. Outboards (even single, with good steering and a "spinner") will allow the boat to run in its own lenght.
