Merits of getting a second master's degree?

Those don't seem like good reasons to me. The only practical reason to get a second master's degree is if it will get you the job you want and it will pay for itself in some reasonable period of time. Are these two conditions met? Or do your life circumstances make an impractical reason feasible? (I agree, go straight PhD if you think that is where you want to go, the second masters will just be extra years)

I am in a field where PhDs are generally unfunded and have poor job prospects, and where some really cool (in my opinion) jobs occasionally require and often prefer two masters degrees. This is not to disagree with the above posters who are certainly correct about their own fields. This is just to say that the answer to this question really, really depends on the field. OP, maybe you could specify your field in a follow-up? The main thing that has helped me reshift the focus of my career in a direction I want to go has not been the grad degree I'm slowly working toward while working full time. Most of my classes for the degree are just hoops I have to jump through to get the credential. If the credential wasn't required for the vast majority of jobs I'd want, I would have just taken a couple of the useful, interesting classes instead of taking everything required for the degree. What has helped are my self-directed projects outside of work or school. These build my portfolio and help me network in the area of my interest. I'd suggest that you take a few hours a week to do some self-directed work in your area. Maybe free online courses that build the skills you feel you're lacking. Maybe keeping up with the academic literature in your field. Maybe some intensive monitoring and analysis of relevant job listings. Maybe informational interviews with people who have the sorts of jobs you might want, or who do the hiring for those jobs. And then decide whether you still need the second masters, or whether you're ready for the PhD program at that point, or whether you want to go in another direction that maybe involves direct application of your skills outside the academic world.

Are you getting funding for these masters degrees? Would you for a PhD? What kind of career prospects do these degrees give you? I would leverage your network as hard as you can do go into a PhD program now, rather than continue racking up masters - there is such a thing as being in school for too long, and it can make you look wishy-washy or like a professional student.

I have two master's degrees. I regret getting the second one. I just recently finished paying-off my last loan, approximately 19 years after I graduated. (In fairness, I also don't think the material I studied was very interesting, so maybe I'd have a different perspective if I had studied a different area.) If you're interested in the subject, study it on your own. Having done one master's degree should have taught you how to do library research. Of course, if your intended field is something like engineering or biomedical research, you're going to have trouble getting hands-on experience if you don't formally enroll in some kind of program.

If you can find somebody else to pay for it, knock yourself out. Otherwise... you're talking about a great deal of expense for negligible return. (I have two master's degrees. Every job I've gotten since can be traced back to connections made in the second program, but it's also responsible for most of my mountain of debt. If I had it all to do over again, I probably wouldn't.)

What are your career aspirations? Unless this is somehow required for your dream job, it seems like a waste of money and time. I don't have any master's degrees, so feel free to ignore me if you want, but I think you would be better off getting some actual real world job experience and work place skills. Getting a good education is great, but people expand their skills and learn on the job all the time. You can take on more debt as you learn and develop, or get paid to learn and develop. I would chose the latter. I also think actually starting your career will clarify what you like doing and what skills you might actually need. What I envisioned in school did not really match up as well with putting my education into actual use -- I understood everything a lot better once I was working in my area of focus for real. I definitely considered extra degrees when I was uncertain about my career path or lacked confidence. I'm glad I didn't let that persuade me into more schooling and more debt. To be honest, your question comes across more like you're looking to delay taking the plunge of starting your career because you want to have been trained for every possible thing -- I just don't think that's realistic. You should have a specific, crucial reason for the extra debt and time you're considering spending. From your question, you don't.

I should maybe specify that I am not thinking of getting a second degree right away. This is more of a "maybe in a couple of years if I am in the financial situation to do so and have given it measured thought and I get sufficient financial aid" type deal. I just would be interested to know others' experience with the scenario of going for a second degree and whether it allowed them to make a change in the focus of their career or opened up new possibilities.

Think about enrolling in a PhD program. You're likely to be funded, and then you have the option of finishing the PhD, or, if you decide that isn't for you, leaving with your master's.

If you're thinking that simply possessing a master's in a particular field will make you more likely to get employment in that field... generally speaking, nobody cares what your degree is in, and nobody will find two degrees at the same level to be more impressive than one. If you're thinking that a particular program might provide opportunities that could help you with a new career trajectory, such as networking with people who will be joining the same field, or giving you the structure to create a work that you can sell/publish... that's not outside the realm of possibility. It'd depend considerably on the program and the desired career. If you're thinking that the actual things learned in the master's will be more helpful to you in your chosen career than getting an entry-level job in it... HAHAHAHAHAHAHAHA no. (Note: all of the above assumes a career path outside of academia.)