I won't speak on the legality being that I have no experience or knowledge there, some snowblowers can definitely work on cobble stone when properly set up with skids adjusted but don't expect the cheapest electric model to cope well and anticipate extra maintenance. I'd be extra careful operating on any hill, make sure you have a good place to blow it without cars, houses, or people getting peppered with the debris they will inevitably pick up in the snow, and I don't see why it would be a problem though. Make sure to educate yourself by reading the manual thoroughly and make an informed purchase if you're going to try.

I've seen pictures of big snows in the 50s where the neighborhood people were all out shoveling their streets. I don't think the city would mind.

People knew the city wouldn't be able to get to every street for a few days so they took it upon themselves to do it. Of course, a lot of people didn't have multiple cars in those days, so there weren't as many cars parked on the streets.

If its going to take the City 2-3 days to get to you anyway to plow you out, how are they going to be there to cite you for anything if you snowblow your own street? And if Pgh Police cant solve half of the murders in the city, do you really think theyre going to waste any resources chasing down the crime of snowblowing in public? Hell, they wouldnt care even if you were 'snowblowing' lines of cocaine.

Make sure you get one that can really throw the snow so you can form the berms in the right place. Also if there are a lot of rocks be careful that you don't throw any of them into your neighbors cars. That will probably make up the majority of complainers of your neighborly help

If you are clearing a public road you won’t be able to “collect taxes” from people. You could ask them for money but you can require it and I doubt you wouldn’t have any legal standing to force them to pay.

Also be aware that you could be held liable for any damage that is done by you or the your blown snow.

Additionally if you end up covering over people’s sidewalks or driveways while blowing you will be pissing them off.

Go for it. The worst they can do is make you put it back lol

Is this the year my next door neighbors finally acknowledge my timely shoveling of our walks or do I finally just shovel my own little bit? I have received cookies once two years ago from the lady two doors down but that's it! It has genuinely irked me this whole time.

It’s definitely illegal and you could get sued for any damage you cause.

While I like your intentions, I can see someone trying to sue you if they slip and fall or get into an accident where you cleared the snow.

If you are considering this get a two stage self propelled snow blower. I have a long driveway that has a very minimal slope, not sure if I'm saying that right but the street end of it is lower then by the house. I bought a single stage blower a few years ago off Craigslist because I was done shoveling snow and while this thing is much better than shoveling I can't push it up the driveway, I have to pull it backwards up and come down again to clear the next path and it's very exhausting.

The worst scenario I can think of is that you clear snow from somewhere that someone is paid to clear. Maybe your neighbor pays someone to clean their driveway or something similar.

The city isn’t going to fine.

Just do it and don’t shoot rocks into anything/anyone.

It's not legal, but as long as you don't damage anything I doubt anything will happen to you. Obviously, you could become a target of a citation and it's up to you if you want to deal with this. They may just give you a warning the first time, who can say? You do open yourself up to risk, and it's gonna take you a long fucking time to move the snow with a snow blower.

Also gotta add, as someone who plows a little bit at work but not city streets, depending on the weather conditions, you want to wait to plow or add a ton of salt right after clearing the street the best you can. Snow sucks to drive in, but you get better traction on snow than you do on ice. IDK if you're clearing the snow if you become liable for the ice and any crashes that follow. And it takes a lot of salt to salt a street. I go through about 12 bags to salt 1/4 mile and a parking lot.