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I give up! Bottom Painting
You said it was a fixed keel, 23''er, on a trailer, right??? You probably have a four pad support and a keel cradle.
If you have a four pad trailer, you should be able to stabilize the boat with a ground mounted support, allowing you to release each pad sequentially to complete the painting under the pads. You can re-extend/reload the pads with a bottle jack.
For the areas hindered by the keel cradle, I take the near empty can of paint to the launch and complete the painting at that time. If you really want to complete this prior to launch, you will need a second support to the one needed above. Jack the trailer as high as the tongue jack allows, position the supports athwartship forward of the keel, and lower the trailer tongue. This should allow painting of the forward section of the keel.
Jack the trailer back up and remove the supports. Lower the tongue back down as low as it will go, position the jackstands at the aft end and jack the trailer tongue. This should expose the back of the keel.
There are things to a look out for, such as excessive hull deflection at the support locations. I generally try to get near bulkhead locations with the temporary supports.
Just did my Cal (Displacement = 7000#) this way. Took an afternoon.