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1. Will I be able (with training) to navigate the 68ft yacht by myself?
Depends how competant you are.
2. Should I buy new or slightly used?
Depends how sensitive you are to cost versus customization.
3. What are the approximate maintenance (Docking/Port Fees, Fuel, Insurance, etc.) costs for the type of yachts in question?
Depends where and how much you use your boat. A new boat will be covered by warranty but will have bugs to work out. Most of the first year expenses will be usage based.
4. Is there anything I should be aware of about Azimut and Feretti boats?
Newer Azimuts are much better made. Ferretti in my humble opinion are over priced with inconsistent quality within the boat.
5. Should I go for a bigger boat, like 78ft?
Insurance maybe the determining factor on the size. Given your limited experience you may not be able to get insurance.
6. What else should I consider before deciding to buying a boat?
Take a boating course.
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