Watched Ben Hall rig his wing sail just that way.It took about 10 minutes and just two people.
That's the only way you can do it with a wing mast I would guess. The A cat and wing mast are also VERY light.
A typical cat would be a huge pain to tip on its side... and then hold it there. Then wire the mast etc. Then lift the heavy thing up.
Naw... not easier on its side in most cases.
Now... if you had a special trailer or...
I do recall the Americas Cup cats when they were in San Diego... one of the 60 foot boats had a wing mast. They had a rack, I would guess was Hydraulic, that would tilt the boat on its side for maintenance or for storage.
http://www.americascup.com/en/acclopaedia/boatdestiny/index.php?idIndex=0&idContent=5171