Bdtyktl

I'm using my circumstances as an example.

I don't have a strong Bachelors (it's in Math this past year) nor three strong letters of recommendation. I am 25 years old in the USA and have not held a full time or part time job yet. I have one volunteer unpaid internship in Hospital Information Technology (mostly blue collar work).

I want to go to a good school in Computer Science to study machine learning, but do not think I can currently afford it nor get accepted. I want to learn some significant mathematic theory in addition to the courses/electives offered in a C.S. masters.

How do I decide from a perspective (either mine or an employer's) whether it is productive to pursue two Master's Degrees back to back?

I am considering starting a Master's in Applied Mathematics focused on Finance/Business at an international university in a year with very low or free tuition (a country like Germany, France, Belgium), even if I have to learn the language.

One year into the degree, I would apply for Computer Science programs in the USA and Canada to study Machine Learning with a focus on Data Science after graduating.

Pros I have read about:
I would have the ability to work part time throughout both degrees to pay living expenses. I am currently debt free. I would have multiple opportunities for internships and research. The programming done for my research would be part of my portfolio if I make it test-driven and production quality. I would learn two important and related skills for Industry. I would have the opportunity to travel. I would be more likely to get a fellowship/scholarship or TA/RA position that waives tuition for the second masters. At the right school, I could try very hard to have a significant part of my second degree be a collaboration with a company / organization to work on an important real world problem in industry together.

Cons I have read about:
If I don't plan it right, this could be unbelievably expensive. Employers would view me as over qualified for certain positions. Employers may view me as a professional student and see red flags. It may look like I failed/dropped out of a PhD program. I would enter the job market significantly later than my peers (30 years old) causing red flags. I can only spend $40,000-60,000 USD total for both degrees, excluding living expenses, over the four years. Some employers may think that I will only be happy in a job that uses both of my specializations and I will get bored / move-on otherwise.

How do I figure out what employers value, and how do I decide what I value from these pros/cons?

How does one determine pros/cons they have over looked? I assume it is worth it to ask hiring managers on LinkedIn how they view the situations and credentials one would have in this scenario?