Career Restructure to DD with 18 Month Garden Leave

I'm a junior engineer at a top hedge fund on an automated trading desk and am interested in moving into a trading role.

I went to a top state school (to the degree that top state-school is not self-contradictory), and have a low undergrad GPA (but above 3.5), with dual STEM degrees. My connections aren't great. I feel my non target background will lessen my career potential years down the line. From what I've seen at my current fund, almost all people in senior positions went to top schools, and all have graduate degrees.

When I leave my current job, I'll be subject to an 18 month salary-paid non-compete agreement. Even if I could land a trading job, I would have to sit out and work at a FANG. As I already have this experience, it doesn't appeal to me despite the double-pay.

The non-compete gives me a unique opportunity to get paid to go back to school. I'm considering a JD, with the idea to work in restructuring law after school, and later moving into DD investing.

I'm specifically interested in an investment role that requires a legal expertise. This is because of my experience working at an automated fund: algos take any easy pickings (eg RenTech) and humans are inherently biased. I don't want to do a job that I think a computer would be better at doing. My view is that DD is currently less susceptible to this. Additionally, I like puzzles. I'm great at combing through code to find subtle bugs - I want to apply this same perception to detail to analyzing financial contracts. For fun I read finance books, having recently finished Moyer's Distressed Debt Analysis, and am currently halfway through Fabozzi Handbook of Fixed Income Securities. (book recs welcome).

My intention is HYS or bust; I wouldn't spend the time and money to go to school if I didn't land a top school that can change my career trajectory. I would potentially consider in decreasing order Columbia, Chicago, and Penn. I plan to have completed CFA levels 1 and 2 before applying.

I think WSO's general advice against JD is wrong for the above reasons. Let me know what you think!

Additional relevant information:

• I plan to apply to school Fall of 2021. I would be 30 upon leaving JD.

• Current role is considered front-office. LTM I've earned over 350k.

• I would need a near-perfect score on LSAT, which is difficult to get. Min 175, targeting 178+.

• I've considered JD/MBA, but feel the MBA gives little value-add. When combined with extra commitment (even for 3 year dual program), MBA ROI is negative.

• My fund fires aggressively; staying here for more than 2-3 years is statistically unlikely.

• I have a strong view that software engineers salaries will level out to over engineering levels over the next 5-20 year horizon (to target ~200k for mid level), dramatically lessening my market worth.

• Fiancée is JD candidate at HYS