OP mentioned the work was on legacy systems, and many of the top jobs that everyone want are likely going to be doing new development with new(ish) tech. I'd imagine especially doing legacy work at a non-tech company will not look very good on your resume to a tech company (whether that be a startup, small software firm, or big n)
> ... doing legacy work at a non-tech company will not look very good on your resume to a tech company...
This, more or less. Maintenance also tends to be a very low-visibility activity at most companies as well. Promotions go to folks who can make a name for themselves working on the company's hot new project.
It took a while to find a job using modern tech when I had a resume full of things like Solaris 8, Ada95, ClearCase, and Oracle. I finally found a company to give me a chance doing new development using modern tech (well, Java, at least) back in 2012 (in my early thirties). My career has been doing much better since, but I feel like I'm far behind where I should be for someone my age (not in skill, mind you, but in pay, role, status, etc).
Just my guess