I single hand everytime....
and used to go in bow first. It was a lot easier to get into the slip that way, but I always had problem slowing down enough and get the boat tied down before either prop walk or wind blew around. I re-anaylized the situtation and realized four things 1) the fact that my boat has a built in bumper near the deck, the bummer matched up with the slip if I came in stern first 2) I enjoy the stern entry of the boat from the dock instead of the port entry from the finger 3) I could use the techneque in the archives where I can dock single handed and not leaving the cockpit if I go in stern first** 4) I seem to have more control of the speed because I come to a complete stop and then back in.** Run a line from the mid cleat outside the lifelines to the cockpit. create a big loop and hang over lifeline. Then run backup past mid cleat outside of lifelines. Bring that end back inside lifelines and to a winch. When backing in, just after the stern enters the slip, reach over and throw that loop around bow cleat on the finger (keep in reverse while doing this). Pull slack out of line from the winch. As the boat moves back, the line will tighten, bring the boat to a stop and pull it to the finger. keep giving slack slowly to allow the boat to back up to where you want it. When you got it all backed up, turn the engine off, hop off and tie off your bow and stern lines and your all done.Now I have to admit, backing is harder, but if you give yourself enough room to get your speed up, you can steer it in on the first try. The trick is to pass your slip up a bit before you stop. If you don't, you will run out of room before you get up enough speed to have steering.