A few responses:
1. “Your return on investment on a Masters CS degree will come over time.” It might produce a positive ROI over time. It really depends on what you do, what you intend to do, and what you value.
2. Re: negotiation. Check out ‘patio11’s seminal text on this subject (other good articles on there as well): https://www.kalzumeus.com/2012/01/23/salary-negotiation/
3. Re: risk mitigation. A robust professional network is almost always more valuable and more resilient than a MS CS. I actually think that this is OP’s biggest opportunity/challenge.
4. Re: Summary of experience. I looked at your profile, and it seems like you’re relatively new here. ‘patio11 is one of HN’s most prolific posters. His posts have declined dramatically in frequency (due to work?) over the past year or so, but he is one of the grand hommes of HN. Check out this link: https://news.ycombinator.com/leaders. ‘patio11 is third, and that’s with a year plus of minimal commenting. Note that I have a very large scrapbook of smart things he has said in HN comments.
5. Remember that leader list, check out #1. ‘tptacek and ‘patio11 actually started a business together focused on the hiring of software engineers. It shut down for reasons unknown, but HN was (largely) rooting for them. It is still not entirely clear why they shut it down other than “hiring is broken” (i.e., employers claiming they want $TRAIT, but demure when a candidate with $TRAIT is presented to them, usually for something nebulous like an undeclared standard for culture fit). Anyway, both of these folks have a great deal of direct and indirect industry experience, and they have a habit of saying very smart things on a regular basis.
6. Re: soft skill limits. Short answer, cognitive biases. Slightly longer answer, first the problem needs to be acknowledged, and then — maybe — it can be solved. There are myriad psychological reasons (e.g, cognitive biases, mental disorders, etc.) for breakdown to happen at any step of this process. Is it possible to attain almost any soft skil, sure. Is it probable? Not for some people.