Should I take the new SAT if I've already taken the old version?

I have a 1940 on the Current SAT and I'm taking it second time this weekend to try for 2000+. However, I also want to get a good score on the New SAT. Would taking 4 SAT's (2 old and 2 new) look weird to colleges considering I'm in the class that is transitioning between versions?

My advice is to reassess your options after you get your scores back from the January SAT. If your score is above 2000 and you're happy with it, you should skip the new SAT and just stick with that number. If not, you can consider taking the new SAT. You may want to wait until senior fall so that you will have more review resources at your disposal (I wouldn't recommend taking it more than once after you've already taken the old test twice).

Since you're already scoring relatively high on the current test, however, I think the new SAT should be a last resort option. Scores will be somewhat unpredictable, so you could end up doing worse on it. Give the last administration of the current test your best effort so that you can avoid the new test. Since you're in the transitioning class, colleges won't judge you for submitting scores from the earlier test format.