I find your (relative) support for night school to be an interesting angle (disclaimer: I am a non-trad considering a night school program, because I am finding my job/career/field is getting moving into an era where law/policy/contract details are becoming more important factors). I am a big fan of the idea that many of the great opportunities in the near future (e.g. next 30-50 years) will be an the intersection of multiple disciplines, and those people that find successful combinations of skills across disciplines can be in a nice position to capitalize.
An obvious downside to this is the amount of time and effort this takes. Not only does one need to develop skills in multiple fields, be prepared to stay relevant in these area, and the need to make and maintain contacts across said fields. It makes me tired just thinking about it.
One generic modification I would suggest to your career advice would be for those people who are starting out to consider things outside their region. There is no reason to limit your opportunities due to happenstance of your current residence.
Yes, I absolutely agree. It seems like you have a solid plan and are looking into law school with a clear objective of enhancing your earning prospects within an existing career while not quitting work for 3 years. MBA programs cater to people like you. I think the night law "stigma" if there ever was one is largely gone and people view it as a smart way to get ahead. It is only an extra year if you can hack working and studying.
the night law people I've met have always seemed to be a bit extra bright and motivated as a group.
I would add to my original advice that you could talk to lawyers and find out what their bread and butter business clients do. Typically, there are far less outside lawyers than people working for the client directly as business people. Often those business jobs are easier to get and possibly pay the same or more.