That's an interesting and useful set of degrees and skill sets to acquire.  A comprehension of markets is very helpful for UD (esp master planning) work, and knowing your way around policy and regulations is useful in RED.  And for both, knowing about building types, how things connect, how big things are, the importance of space--via architectural training-- is beneficial.  So, intellectually and academically, that's a trifecta in my mind.

But I'm wondering: what you want to do/ where you want to work?  RE firm?  UD firm?  Public agency?  You'd probably be qualified for any of those, since you'd've covered all bases.  As for ROI on yet another degree in terms of additional salary dollars?  That could be the point where the law of diminishing returns rears its unwelcome head.

(My two cents; your mileage may vary.)

As far into the future as I can see; My end goal is to own and operate a small development firm. One that focuses on bridging the gap between the development and design processes, thus creating more successful, engaging, and speedy developments.

I am interested in Urban Design more so than Architecture particularly because I see it as more of a profession, rather than an appeasement of my own residential Architecture curiosities. I know in my early career, I will inevitably be drawn to cities to find work. Whether that means I find that work at a RE firm,  an Architecture firm, an Urban Design firm, a REIT, or a Bank, I have yet to find out. However, I do expect to primarily use my Real Estate Degree initially, and finally. I would love to put my (potential) Design Degrees to good use, as I have a huge passion for design. However, it seems to me that my efforts may be best focused on Real Estate with some design work sprinkled about. 

As far as the ROI goes, I do in fact see the short term financial opportunity cost of pursuing another Masters degree as a loss. However, I also see my ability to acquire a job (Perhaps a better job) by achieving two interconnected specialized Masters Degrees as a win. Doing so would also culminate my own personal academic ambition.

Thank you for your comment. I have done much reading on this website's forums and have come to respect and appreciate your input!

Thanks for the kind words, crafty.

Good luck, whatever your decision.  The world can use a lot more well-informed developers.

All input is appreciated. I could really use some more advice regarding the ramifications of acquiring a pair of degrees such as these.