Our school district pays for all 9th-11th graders to take the PSAT. Middle kid is in 12th, so she won't be taking it (I think the seniors are watching The SpongBob Movie during the PSAT).

I don't see any harm in taking it - it will give him a preview of the new SAT. Since colleges don't see your score, they won't judge him on his PSAT performance. And if he is a junior and does well, he could be NMSF (some schools offer NMSF/NMF great scholarship opportunities).

I think it is a good idea to try both the old and the new SAT. If he is a 2017, most colleges will accept either the old or new SAT with his application. If he is 2018 or beyond, take a look at college policies. Some will not accept the old SAT for HS Class of 2018 or later.