I recommend getting a charter captain who is willing to teach. My wife and I did that last year (Captain Juls out of the Port Clinton area) and it really helped. Research here to decide what kind of trolling you want to try then find a captain who will show you how to do it properly, not just set everything up for you and have you reel them in. Juls taught us how to run planer boards and crawler harnesses, and it was well worth it. But make sure you get someone who is willing to explain why they are doing what they are doing. Well worth it in my book.

On our boat (20 ft Grady White walkaround) our goto method is trolling crawler harnesses with inline boards, we use bags to slow us down but I'd love a kicker. We also pull crankbaits behind the boards.