I would not like to do the planning and coordination of multiple ships and itineraries to accomplish continuous retirement living aboard.
I'm not sure about how last minute Last Minute Cruising can be now due to regulations implemented after 9/11. We have a home Carnival ship here and have asked about last minute boarding deals. We were told there were none as there has to be a certain period of time for one's passport, etc. to be checked out. I think they said a month to three months. Yet I met a lady who was aboard a ship out of Cape Canaveral, FL, who said she does it from there.
Does anyone here cruise on really last minute deals? A week's notice? Two?
They definitely still have last minute deals. I checked NCL quickly and there are multiple options leaving May 3rd. I think it would be impossible to organize that to arrive and depart the same day. If you wanted continuous cruising staying mostly on the same ship would make sense.
But if you had a home base in a major port city I think you could get lots of last minute deals and spend a big part of your time cruising at a discount.