I like the analogy to a pool. As much as I like to swim, I wouldn't buy a house with one, but that's just me.
Last year was our first season with our Catalina 350 (all of our sailing had been on our Seaward 25 and Hunter 23.5, before it). The difference, of course, is that you can often muscle a 25' boat when things get dicey at the slip, but that's not possible with a 35' boat. The marina we were in was basically set up for power boats. Large marina, tight lanes, a starboard tie (this boat will not back to starboard), and worse, a large unforgiving steel pole between adjacent slips at the stern, but not far enough back to clear the boat.
Getting the boat in was dicey, with that pole. If you tried to reverse it, you would hit the pole when it walked to port. We usually would spring the bow in and stop it with a docking stick at the center cleat, however sometimes this went wrong and the stern would kick out before I could get the the stern line in place. Again, the post! Backing the boat out was only possible by springing it out from the corner of the dock...had to back to starboard to head down the fairway forward (in a pinch we have backed it all the way down the fairway...embarrassing but who cares).
We never had enough time to develop a foolproof set of tricks as we spent much of the summer cruising up in the Great Lakes away from the marina we had learned to hate. After more than 1000 miles of cruising without incident, and quite a few nights in other marinas also without incident, we made it back to our home marina only to ding the port stern corner of the boat on that friggin post.
Enough was enough...we changed marinas late in the summer. No more post and a roomier slip. Problem solved.
We would have died for a bow thruster in the first marina, but kinda like a pool, I wouldn't have paid extra for one when we bought the boat. I sure would consider it a nice extra though if the boat came with one and we wouldn't hesitate to add it to our bag of tricks.