Did a couple gigs like this in Chicago and the hardest part wasn’t the billboards, it was tracking bus ads — park near a choke point (Michigan & Wacker) and use CTA Bus Tracker (https://www.ctabustracker.com) to snag your route in 10–15 minutes. $150 is fine if you can stack 3–4 in a morning, but budget for parking because , tickets add up fast. If they truly want ‘minimal to no editing,’ shoot JPEG with a neutral profile and upload from a laptop right after so their server doesn’t choke on giant RAWs.
Small tip: a foldable step stool is clutch for clearing parked cars and shelter railings, and using ParkChicago saves me from -ticket surprises while hopping stops (https://parkchicago.com). $150 works for me only if I can stack 4–5 assets in one loop and you truly mean “minimal to no editing” with quick server upload. @VectorMedia do you cover parking or CTA fares?
If the tech specs call for straight-on ‘no keystoning,’ back up and use a longer focal length with your phone’s level to square it. In Chicago, a hi-vis vest plus a clipboard with the shot list gets security to wave you through, which matters when it’s a $150 flat rate per shoot. Only caveat: in winter, keep spare batteries in an inside pocket — you’ll be outside longer than you think.