and is there really NO compromise that allows marshall and lily to both do what they want? Marshall could be a judge and visit lily several weekends a month.
The captain is incredibly rich and values lily enough to move her to rome- why does she even need to move completely? Why can't lily go to rome for, say, half…

In the 8th season, didn't marshall apply for a judge position in the episode, "Twelve horny women", and lily became the captain's art buyer in the episode "the ashtray" several episodes later? Now I do recall that his judgeship interview with fat. mr belding was a flashforward, but he still applied to be a judge…

and don't forget to mention the shots that opened up the pool scene at the end- it wasn't a complete recreation of the black and white teddy bear scenes but it was the same thing- 
a close up of a dripping hose, 
followed by a close up of a hanging ornament blown by the wind,
and then a bug crawling across the stone.
 …