There are other issues which would arise, if you began to alter the ship, in order to make her fit to go back to sea - paying crew would expect toilet facilities / showers / modern galley / decent (private) sleeping quarters. I doubt very much if (per capita) short 'voyages' with a relatively small number of paying crew, would bring in the revenue required to keep up her maintenance programme.

Not sure if she would fall within the DDA (Disability Discrimination Act) - if you began to make such alterations, it might well be that the whole vessel might have to be altered to be able to accommodate wheelchair users

... nothing is as simple as it seems

There are already plenty of ways to go to sea in a sailing vessel, which will already have all the necessary acoutrements for safety etc. I see no real reason to, effectively, chop an exceedingly rare surviving ship up to provide another. This vessel should be preserved for future generations - I don't think our desire to say we've sailed on the Cutty Sark is a good enough reason to 'bring her up to date' in the ways which it would require.