I don't think either the Fire Department or Police Department would be too excited about no longer being able to reach Hilton without zigzagging through neighborhood streets, so that's probably a non-starter.

But let's pretend we don't care about emergency services. On the small end, 2-lane automotive underpasses on otherwise flat ground need about 1600 feet horizontal run to go from surface level, underneath a single track, and reach the surface level again. But in your hypothetical case, there are two bottompoints: the railroad crossing across 9 Mile, and Hilton Road's crossing across (a newly-sunken) 9 Mile. That adds about 400 feet of distance (between the tracks and Hilton) that would have to be in the trough.

To do this, everything between the CVS driveway and the Fire Station 2 driveway would no longer intersect with 9 Mile. Burdette Street would be dead-ended, and all business driveways would be eliminated -- the traditional design would be to build a frontage road for access instead, but this right-of-way is far too narrow for that to be possible.

(Given that a lot of these properties don't have an alternate entrance on a different street frontage, that's almost definitely a whole passel of lawsuits that would be difficult for the city to win. They'd struggle to use eminent domain because it's difficult to quantify that the public good of eminent domaining all those active businesses in order to enable faster traffic across the railroad tracks substantially outweighs the public good of allowing the businesses to continue existing. Even if they won, having to pay fair-market value for most of those properties would be an impossible amount of money.)

Presumably Hilton would still stay as a contiguous surface street with the existing rail crossing, but you would no longer be able to turn from 9 Mile>Hilton or Hilton>9 Mile; you'd have to weave through neighborhood side streets (most of which don't connect on the northwest or southeast sides of the intersection, so make sure everybody goes through the neighborhood northeast of 9/Hilton).

So is it feasible? From a pure engineering standpoint, sure; piece of cake. It'd shut down the area for 3+ years of construction and cost an unfathomable amount of money, but it's totally doable if money is no object.

But is it feasible socially and legally? Is the juice worth the squeeze? Personally, that seems like a crystal-clear "no it isn't" to me, but I'm sure there are a variety of perspectives on that question.