Boats for chartering and charter insurance need inspected/surveyed which costs plenty. If they dont pass this insp. spend the money a fix all the items then see how bad they hit ya for ins. Older and some newer Sportcrafts will need new stringers and sometimes the stern/transom is rotten. Some Baha Cruiser have transom issues also. You need plenty of water time over 5 year period on great lakes and /or western rivers. A month of weekends of class and then pass a near day long test. Lic fees, countless gear, safety gear, and this is just the start. Figure out what you would want to do when you get the license. Fish, touring, boat transfers, sailing trips, yacht charters, oil rig boat crew. 1 to 3 person fishing trips, 4 or full 6 person aka 6pack lic. Get your masters for more than 6 people/ recommended ! I went thru Sea Tech Marine training out of Buffalo NY. They teach you instead of just tell you enough to pass the test. The basic lic for the great lakes area would be the 6 pack for Great Lakes and Western Rivers of the US for up to 6 paying passengers. Dont worry about the boat first.