I've got no advice on non-draining beds. But Tranoble was getting great results and if you have a good grasp on that concept, go for it.

If you use OSB I'd line it in plastic just to keep the plants and the glue from coming in contact. Why? Just a hunch.

HAve you priced out actual plastic grow trays? By the time you're done with all the other building hassles, and buying materials, it might have been better just to buy a tray. Although you are urban, and rubbermaids are WAY more stealth to be carrying in and out of your apartment. Your call.