If cash is an issue (or even if it’s not), you might want to go to the local yacht club and see if anyone needs crew members. It’s worked for me on a few occasions. There are a lot of people out there who have big sailboats and are willing to teach you in exchange for being able to take their boat out more often. Sailing might not be your ultimate goal but it will get you experience and help you do some networking for crew jobs in the future.
As others have mentioned, becoming a DM is a great idea and getting CPR/First aid certified will also make you more employable.