Low Wing instructor?
that depends on you.. and the type of low wing plane
But since you asked I'd say it wouldn't hurt to have a more experienced flyer maiden it an trim it out then maybe a flight or two with them nearby or on a buddy box..
Then agian if you have mastered your trainer and are Confident in your skill you might be fine... all you have to lose is the plane!!!
Not much of an answer was it!!!
BTW it wasn't a stupid question... If you feel you need the help ask...