For all the development that has taken place over the past 10+ years in the W Loop, there's still a need for more Commercial and Retail businesses to establish and add more vibrancy to the area. Yes, there are great restaurants along Randolph street and a great deal of new businesses have come into the area and added to the streetscape but too many midrise buildings with garage structures have rendered vast swaths of street unfriendly to the pedestrian and casual visitor. Walk the streets bounded by Halsted, Randolph, Aberdeen & Monroe and you'll get a feel for the area.
Street vibrancy is a great indicator of a neighborhoods potential. Take another walk on Division from Ashland to Damen and then north on Damen to Armitage and you'll see street vibrancy. Observe and compare each area and decide which has more upside potential over the next 5 years. I think we'd both pick the same area.
Best of luck, Ken.
I have a good friend that lives in the West Loop right off Washington and Canal Street. He loves it there!
Good luck in your home buying efforts:) If you have any financing related questions please email me at Tino.Muratore@gmail.com. There are quite a few home buying incentives if you purchase your property downtown Chicago.