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My presumption is it doesn't matter who my Recs are, but wanted I wanted to get some insight anyway. I only need two, but can't see that it will hurt to get four.

Any of these look like slam dunks or obvious missteps? TIA

1.JD/friend that repped me in a criminal case - relatively old DUI, disclosed in C&F
2.JD/colleague I've worked with for 7 years in transactional support roles
3.JD/Prof. of Negotiation and Dispute Res. class I took for Masters
4.PhD/Prof. of Global Finance Regulation class I took for Masters
5.UG Prof./Advisor
6.Masters cohort/colleague

These are recommenders for a law school application? Do NOT use the friend who repped you in your DUI. If by masters cohort/colleague you mean a fellow student, don't use them either. You want mostly profs, assuming your work for them was fairly recent, though the work colleague wouldn't be bad (assuming they had some kind of supervisory role and reviewed your work, which is what it sounds like. If they're just a co-worker then no, don't use them either). Basically, you want people who have been in a position to assess your academic or professional work.

(You're right that it doesn't matter very much, but some recommenders are still better than others.)