I have my 100 Ton with a sailing and towing endorsement. It saves me a few dollars on my own insurance actually. Since I don't use my own boat in any commercial venture, my insurance went down. As far as the "list" of hurdles that cost a lot...not so bad. I have the TWIC card. There are locations for that all over. They take a picture and use a thumb print. Took one 15 min. visit. I can't remember the cost, but not much. I do "minimal" deliveries...1-2/mo. It's basically for fun. The fact that if you are a passenger and can be held liable is wrong. If you aren't being paid as the Captain, you can't be held liable however, IF you are being paid, you can be held liable. That is why insurance companies want a paid captain. They can defer responsibility to the Captain. I've found my license is a "little" profitable based on what it costs to maintain one.