Trailer sailer conversion

[Rhaduznt]

I am new here so if I bend the rules a bit, a polite explanation would be appreciated.

I am trying to find out how much of an ordeal it would be to convert a 27 to 30 foot boat with a keel stepped mast to a roof stepped mast that is easy to lower for trailering.

I have asked Google but contrary to popular belief, Google doesn't know everything.

[Montanan]

Youtube has videos of deck masted sailboats with creative raising and lowering configurations to facilitate trailering.