Personally I think what he's interested in or excels at is going to be what opens up opportunity. CS job market is an absolute wasteland in my almost 2 years being conventionally unemployed with engineering degree and experience. There are tons of "openings" in web development, but mostly being filled with senior positions, or filled with AI currently. Also really depends where hes located or wants to be located. I've heard local/in-person hiring is the only way to really get in. Experience in something niche is really going to help and he should run with it. Like if he has any knowledge of the inside of any industry.
Degrees (especially masters and beyond) really help get you tucked nicely into government work. US government (and contractors) strictly hire off degrees. It literally determines your position and your pay ranking. You cannot get hired without proof of a degree. BS really won't get you far in terms of pay, and from what I've heard you can't move vertically without a higher degree which is why most government employees go back to get a masters or more. I know some that went for the fastest and cheapest masters just to get into the job they were qualified for but weren't allowed to do until they had a masters.
That said, again unless there is some kind of niche (and especially if you know someone in the industry hes interested in) it's not gonna be easy, and TBH im not sure id want to spend the money for no better chance of getting hired in the field I have over 7 years experience in, even if it's very unconventional.
Consider finding some tech hot spots, like Boston, Nashville, Morgantown, DC/Nova/Ashburn area. I've heard Austin, Silicon Valley, Denver but never been. I had some chatter in Detroit but never made the interview. I've heard some guys in tradfi are pretty unaffected by AI right now, but that's only a matter of time. They're really looking for in-office these days, so he may want to save up to try out some of those locations and see where he wants to live.
