first of all you know what free advice is worth ? so take it from there, I have a 26S so have no experience on your model. However I think the dagger board will have some taper to it so it would be best to take it out from the top as it is all the way up and is on the trailer. You may need to use a small jack on the ground to apply pressure and or a "come-along" from above. If you can supply any form of lubrication that might help, a good choice would be dish soap, can't do any harm and easy to clean up.
good luck, Bob