thats going to be a tricky maneuver no matter how you do it.... and I would think getting back in would be worse.
if I HAD to do it, I would have a line long enough to be cleated at the transom cleat, then ran thru a spring cleat on the dock, then around the bow cleat on the boat and back to my hand. with a bit of extra left over.
so now.... if it is tied to the transom cleat then ran thru the hole in the spring cleat on the dock, then AROUND the bow cleat and back to you, you will have quite a bit of fore and aft motion and still be connected to the dock.... IF you dont let go of the tail end that is in your hand.
as you move rearward, the bow will stay at the dock rather than swinging into the neighbors boat because now the spring cleat is almost even with the bow cleat and held there by the rope in your hand.
you said you had no trouble with the stern getting away from you because it pulls into the dock. so now as log as you can hold the tail end of the rope in your hand, and you have paid out a bit of line as you backed out, you should be about out of the slip and backing around the end of the dock finger. at some point you are going to have to let go of the rope and let it pull itself around the bow cleat and thru the spring cleat while you run to the stern cleat and haul it in so it doesnt foul in the prop. you should have about 10 seconds to haul in the line and get back to the helm before there is any immediate danger from another quarter that you will have to struggle against, but with practice you will soon be looking for other, harder challenges to conquer.... like getting back into the slip under the same prevailing winds and currents, without any dock line assistance..... or an even harder challenge, like trying to find a different slip that doesn't give you such difficulties when going in or out.... best of luck to you.....