Congrats on being debt free, that's a great feeling!
Both my sisters have two masters degrees each, my younger sister has a masters in both biology and chemistry. She works for me as my warehouse manager, she's more valuable to me than the job she was working in a lab and I pay her significantly more. My older sister has a masters in health administration and her MBA, she actually works in IT for a very large insurance company nothing related to her masters. Mind you my older sister barely knows how to turn a computer on she just knew the right person and they offered her a job. She actually does really well at her job considering she barely does anything it's totally an adult daycare job....remotely from home no less.
I have a degree in accounting, I've never worked as an accountant a day in my life and I quit in the middle of getting my CPA because I realized how pointless it was. I was sitting in an auditorium of a small university with a very small business program with at least 100 other kids all going for their CPA, there were multiple times a week for this class and more than one professor. So this small university was pumping out probably a thousand CPA's that year, how many colleges are there in Michigan? How many throughout the entire country? How many CPA jobs were opening up that year? It just didn't make sense anymore, I was getting a degree just to get it at that point putting my actual life on hold so I quit and started a business. Not to say you should go and start a business just putting my decision into perspective.
I think you have to look at the time and cost vs what you will get out of it. Make no mistake you're putting your life on hold for assumingly a couple years plus the cost of the schooling, would you do better POSSIBLY finding a job with the masters or would you be better off with the two year head start and money in your pocket? I think if you were already in a position and they told you "get a masters we'll bump you up" that's different but to just go get a masters and then blindly go job hunting at the entry level I think the years and money are more valuable than that. In the end you know better than anyone else as there are multiple subjective variables but be wary of falling into the trap of the "I'm in school" excuse when in reality you're just putting your life on hold, especially in your mid 30's. I know a lot of people who fell into that trap and all they were doing was delaying actual progression in their life seeking the easy path.