Last I understand, you will need a live job offer before you can qualify for a TN visa. I think that's more important than the degree since you already have one

Last I understand, you will need a live job offer before you can qualify for a TN visa. I think that's more important than the degree since you already have one even though it's not in CS. My advice is for you to contact an immigration lawyer and get the qualifications to start. Also, take the time to solidify what you want in your career before you decide that you need more school. BTW, don't expect to have a tech job all your career. As you get older, employers look for younger candidates. Some deny that but it's a reality not everyone wants to face. Plan for that. From my point of view, experience is way more important in a job search than a CS degree. A CS degree guarantees you nothing, in terms of a job, since you get a general education in CS fundamentals. You will need more knowledge to get a job unless the employer is willing to train you. A master's degree is very limited as a way to get a better job in tech. You only need it if the job requires it. Teaching is the only job, I can think of, where it might be needed.