If you want to make yourself stand out, then I recommend against "staying in school for as long as possible" or a "5-year masters program"---five (5) year masters program?---and accomplish something in the private sector.
If you have a network in real estate, then why not get your broker's license and do commercial leasing or something?
When I was interviewing right out of law school and, earlier, business school, invariably I would be asked about how I managed over ten million dollars in property at twenty-one years old. To this day my experiences have helped me in life and business.
I formed my first company as a sophmore in college. I also formed, and later sold, a property management company. If you have a network in real estate RIGHT NOW, then obtain your broker's license and form your own brokerage? You have to check state licensing law and may have to partner, in some form or other, with a "managing broker."
I AM WORRIED
My worry for you, based on world experience---and of course everyone's experiences are different---is that more education will not help you (at all). But if you insist on more education, then why not obtain your broker's license now and work at least part time while pursuing another master's?
I know MIT has an excellent graduate program in real estate.
Most of all, and I mean absolutely most to all, I sense you could be very successful in real estate in some capacity or other. My worry? A law degree could hinder your success. Many commercial brokers I work with have law degrees---and many have no degree at all---and do not use their law degrees. You could still work in real estate succesfully with a J.D., but I think it would only serve to delay and possibly even hinder your success.
Start working now. Get more involved in working if you already are working. You are way too smart to go to law school.
During law school, I was flying to Paris. This was over my second year during the summer. Next to me on the flight was a kid around my age. His dad was a retired football player, and I was able to learn about the football players' pension system (still find it interesting). His dad was successful after his football career with varied small businesses: gym, laundry mat, etc.
Anyway, this kid tells me he basically has a career lined up in professional baseball. I do not remember the full details, but he was going "pro" or "majors" or something. But! He told me that he would give that all up to practice law.
I told him honestly and sincerely that he was not smart enough to practice law or survive law school. If you had a shot at becoming a professional baseball player but would rather pursue an uncertain legal career, then your ability to solve complex legal problems is not there.
We hung out a bit in Paris---his hotel was right down the street near me, and but for him I would have gotten lost to my hotel---and I am not sure where he is today. I honestly, sincerely, truly hope that he is a successful baseball player. Now that I think about it, I should have said, "pursue baseball first and if that does not work out, go to law school."
I WANT YOU TO SUCCEED
I warn about law school because I want you to succeed. If the (limited) opportunities that law school provided were not so out of proportion to the costs/expenses/time, then I was say just take the risk. It is not a limited risk that law school will hinder your success. My opinion, and simply my opinion, is that it will in all likelihood hinder your professional and certainly personal (financial) success.
Edit: If you do not do law school right, a J.D. is going to hurt you in many and varied ways, professional and personal.
Edited by ShoeShopperJ - 5/13/12 at 7:45am