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Re: Things that make you go "Hmmm...."
Take the summer and apply for jobs outside of teaching just to see what you could actually get and what you would actually get paid, (remember that the real world folks for 50 weeks a year). You might be surprised at just how many jobs you wouldn't get because while we as band directors have skills that translate to other professions those hiring folks don't always agree.
Teaching has its downsides but teachers also have it pretty good in a lot of ways.