I am an advocate of stern first IF your boat is good at going backwards. I do not use piles but if I am coming into a wharf (to windward) then stern first is much slower, safer and secure than going in forwards.
We were doing the usual forward entry process and it would always be slightly stressful to get someone on another boat or a jetty. Our bows (cat) blow away from the wind
pretty quickly so I had to approach quickly and then stop quickly. Parallax error and distance also meant that I had to lots of variables that made the whole process rushed. Sometimes it meant my wife was jumping off the bows when she wasn't all that happy to do so. On my own it required a lot of effort and running.
Deb told me that she had seen people coming into jetties or to other boats stern first so we tried it. I pull the boards up so the bows will blow away even quicker (I don't come into jetties that are downwind - I use the dinghy) and then head
to the jetty (or other boat) and then do a hard turn next to the jetty so that I am pretty much stern on.
The great thing about approaching stern first is that I have stern steps and nice deep rudders at the stern. The boat likes to blow bow downwind so I can use minimal throttle and back up to the jetty. I have no parallax error and can see always see the gap between the jetty and stern. Because the bows are already blown off the boat just creeps back as I use throttle. Remember that the wheel
must be turned the opposite way than when going forward.
I can truly get to 5cm of where I want to be and on my own I just step off with a rope and I never have to run or jump. I think it looks pretty impressive to do solo. To get alongside the jetty I use some forward throttle after the stern line is attached and the boat pushes itself parallel.
I think the stern approach would be really good for any object that you want approach with high precision if you are not going to be held by the bow after the approach (picking up a mooring). I don't use piles but I would use this approach first before going bow in. It is incredibly safe, precise and damage free. I think approaching the windward pile stern first would be the safest and least stress method for a boat that reverses well. (Also a nice wide transom free of dinghy davits
windvanes etc would help)
boats might not steer well in reverse. Boats with spade rudders usually do. Have a go, it is a great trick to have in the toolkit.