I updated the OP with what I've compiled, including the first stab at a Startown generator.
Here's a test run of the generator. There's lots of room for improvement, and hopefully streamlining.
PROCESS
MAIN DRAG. 1D roll = 5. There are 5 streets giving off of the Main Drag. 1st, 2nd, and 3rd streets are arbitrarily placed on the right.
1st Street. North 1D roll = 2. Two buildings, one at the corner. South 1D roll = 1. One building at the corner.
2nd Street. North 1D roll = 4. Two buildings north (one at the corner), two buildings on Red Zone 21st street, at an angle north off 2nd Street. South 1D roll = 4. Two buildings south (one at the corner), and two buildings on Red Zone 22nd street at an angle south off 2nd Street.
3rd Street. North 1D roll = 3. Two buildings north (one at the corner), and one building on Red Zone 31st street north off of 3rd. South roll = 4. Two buildings south, one at the corner, and two buildings on Red Zone 32nd street south off 3rd.
4th Street. North 1D roll = 3. Building on the corner, building Off-Main, and one on Red Zone 41st street north off 4th. South roll = 3, same results (Red Zone would be 42nd street south off 4th).
5th Street. North roll = 2. Building on the corner, and one Off-Main. South roll = 3. Building on the corner, one Off-Main, and one on Red Zone 52nd street south off 5th.
Okay, I've got a zoned map. I can fill in whatever I want, but as I'm testing out my random tables, I'll roll for every spot.
RESULTS
I'll start with the Main Drag, which suggests there are 10 buildings, on corners where the Drag meets the Off-Main streets. From there, I'll do the Off-Main streets, and end with the Red Zones. The buildings and their locations are:
Main Drag:
Taxi service near extrality line.
Main @ 1st: Casino north, Greasy Spoon south
Main @ 2nd: Bar north, Greasy Spoon south
Main @ 3rd: Trade factor north, Bar south
Main @ 4th: Street vendor outside bar north, Bar south
Main @ 5th: Mass transit station north, Casino south
Off-Main:
1st Street: Used vehicles lot north
2nd Street: Arena north, Bail bonds south
3rd Street: Food kitchen north, Very greasy spoon south
4th Street: Bad hotel north, Bad bar south
5th Street: NEW equipment shop north, Bad bar south
Red Zones:
21st Street: Brothel nw, Bad greasy spoon ne
22nd Street: Equipment shop + Grifter, Mission
31st Street: "Tattoo" parlor and implant shop nw
32nd Street: "Zoo" sw, Loan Shark se
41st Street: Crooked Casino nw
42nd Street: Crooked Casino sw
52nd Street: Truly ghastly hotel sw
GIVING DIRECTIONS
Now (theoretically) a passerby could give directions to players to these locations.
PC "I'm looking for the Roasted Kian... it's a bar in Startown..."
NPC "Yep, it's south 4th Street off the Main Drag. Can't miss it."
-or-
NPC "Uh, yeah, that's northeast 21st Street, and are you really sure you want to go there?"
PC "Well... can you recommend something better?"
NPC "Sure can. Head to south 1st Street, the food and... ambiance... is a bit healthier."