With my trailer, the only way to fully remove the keel is to put the boat on supports and move the trailer away from the boat but......
You can also use the trailer to lower the keel. If you lower the tongue jack and then put substantial support under the stern of the boat, then when you raise the tongue jack again the stern will lift off the back of the trailer. This raises the keel area a few inches and gives you better access. I have 4 threaded rods 12" long that are the same thread as the keel bolts. With a not on each rod, I remove the keel bolts (One at a time) and replace with a threaded rod. Then, I can lower the pivot end of the keel slowly and safely. I have made supports that are similar to cwkwmp's pictures above and when I lower the keel, it is supported by blocks so that the keel can't flop over. It's heavy and weighs in at 550 lbs (Not 500lbs) The threaded rods are a good idea because after working on the keel, you can more easily locate the keel bolts back into their threads as the keel is lifted up again. (That can be a PITA if the bolts don't go back into the threads). Part of the issue with the pivot pin 1" in diameter is that the keel can flop around just a bit. When sailing in waves it may make a clunking sound as it shifts from left to right side. You may notice this some if the boat is on the trailer by how far the keel can rock side to side if it's hanging by the pin and the cable(When that's fixed). This can be eliminated with the hole in the keel being the correct size and the pin not being worn but also you may be able to add some shims to the sides of the keel so that when it's down, it rocks less.
All of this stuff seems like a big job but if you are going to be trailering the boat, it doesn't have to be done very often. Threading this eyebolt is really a one time job for example. CD suggests replacing the keel bolts rather often but that can be done one bolt at a time without dropping the keel. Part of the reason is a safety precaution. The suggested method of trailering is to lower the keel on the trailer BUT if the hull shifts when it's on the bunks, it can strain or break the keel bolts. Of course the prevention is to strap your boat down well to the bunks before moving it.
I keep my boat in the water for the summer and I have to replace the cable & turning ball every other year or every year depending on the summer conditions at the dock. Because of shallow water, I can't keep the keel full down all summer and this causes the cable and turning ball to wear faster.
When I first got my boat, it all looked good. I put it in the water right away for the last month of the season. But the turning ball had a flat spot and had almost sawn through the cable. I think that it was down to about three strands of wire left. That was dangerous. Also my wood bulkheads inside were rotten and loose because the upper chainplates leaked rainwater into the cabin. I've replaced them and sealed the leak where they come through the deck w/ silicone. This silicone sealant works well enough because the boat can flex just a bit at this point.