I've struggled with cityscapes, possibly for the same reason. I've always preferred quick sketches so a detailed city would take too long. but I'm starting to finally get the hang of longer drawings, so I might take a step into background at some point. Or just use sketchup to block it out lol. It's surprising, but I am actually very patient, but only when I think it is worth it, and my art hasn't been worth it yet haha
great themed piece. yeah I think the background could have had a little extra detail, even in the blur, as the blurry bit is quite indistinct I couldn't tell it was meant to be buildings I thought it was more like trees and stuff. maybe more vertical and horizontal lines will give it more of an artificial feel. You can always take the composite route and paste a photo of a city in and blur that, or use it as reference/trace it. I want to try that anyway for fun :P
I like the shading on the clothes and body, but in a few places it feels a bit patchy, or your style is just a bit looser for this piece. good perspective on seeing the bottom of the umbrella but the top of the railing :P I love the shorts because I can't draw shorts yet :)
the tedium just broke me so I blurred everything and called it a day haha.
That's gonna happen but as long as you keep pushing the boundary you'll get there!! Your work is always of a good quality, so if you've made it this far with characters, backgrounds will be a cinch :P
something that might help that I have just discovered being a noob artist myself, is to keep a bunch of WIPs and work on them when I feel like it, alongside my other stuff. So when tedium kicks in, stop and go onto something else. that way you are always giving stuff your best, and avoiding that tedium which can damage your work :P
You might already do this tho :P