Should I wing the first season and see how I do, or should I just hop right into lessons so I don't form any bad habits right off the start ?
I suggest a mixed bag. I wouldn't go into weekly lessons right away if you're only getting out once a week. Best thing I've seen is an early season lesson to start you out, then board for a month and try to learn on your own, then have a mid-season lesson to get you over the next plateau, then an end of season lesson to hopefully tie it all in and reinforce the positives before the summer.
My GF essentially did this, taking 2-3 lessons a year for the first two years. I've got videos to show how she's progressed in that short period of time. She's clumsy, gets discouraged easily, needs praise and coaching from an authority, etc. and lessons really helped for her.