NO
At 550lbs. and near darkness this is a no go. a rope or web strap that will span the bottom of the boat is the answer. Start at the front and work it back catching the keel, attach it to both winches then slowly raise the keel. Watch for a slip off. Once you have the keel up a bit work the boat onto the trailer. Crank the boat on the trailer, change the cable. You might also want to look at the hose, hose clamps, and turning ball. If worn change them out at this time as well. I'd also look at the keel trunk in the port hold where the keel locking bolt is, making sure there is no cracks in it. Good Luck