A quick reality check, for a 200GT vessel, you will need full time crew just to maintain the vessel. Might as well hire a captain/stew team. Nothing to keep you from driving and all the legal an insurance requirements are met. Without a full time crew, your maintenance bill will be astronomical. Plus it expands the usability of the boat since the crew can do repositioning without you onboard. Outside of that, you can get a Yachtmaster and flag the boat Cayman. Also, for the Transport Canada license... Typically there are multiple 1 and 2 week modules involved with STCW licenses. Is there a way you can do those modules one at a time or even through a Distance Learning program?