“Everything about being a single guy willing to come over and teaching English on a lark after college has gotten so much more complicated since I’ve been here longer.”
* Well said.

“I haven’t gotten back to getting more education or gotten specialized. The master’s degree course in ESL at my previous employer seemed like a joke, and I don’t really want to throw money away on another paper degree if I can’t use it practically.”
* I had the same thoughts a few years ago. Going to graduate school seemed like the only way to improve my career, yet it also was no guarantee — and I couldn’t see spending that much money on something that didn’t have a guaranteed result. So, I kept working with an eye on finding better jobs through people I met, and it’s worked out for me.
My advice to you, if you don’t mind my giving it, is to get yourself a small class or two at a company and start teaching business people. Then you’ll be mixing with a crowd that can lead to good contacts and better things. Your students will be a source of help in your career.
When I first came here, the idea of teaching Business English was anathema to me — I didn’t have the training and it sounded boring. It didn’t take me long, though, to find out that Business English is not much different than free talking or conversational English, just that your students are talking about their jobs. You can create the course however you want.
I can tell that you are an imaginative guy. Start branching out from teaching kids and I think you will do well.