If I were you, I would be hiring neighborhood teens to do the yard work and shoveling. They work cheap, appreciate the money, and you will have your work done with no backbreaking for you. I often happily pay either my own kids or neighbor kids for this sort of thing. It encourages them to be motivated and enterprising. Your neighbors will appreciate it (not that that matters much), especially if it’s their kids being hired. You don’t say that they complain about your snow; that’s an issue for your own safety, not to placate them.
By the way, It is not out of line for others to question whether digger is understating his level of unsightliness. I have neighbors who often say, “oh, my yard is a little out of control, but I (insert excuse here).” Their yard is filled with blackberry brambles and rotting falling-over fences blocking the sidewalk, forcing kids to walk in the street. Another neighbor hasn’t done a thing in his front yard in three years, hasn’t stepped into his back yard in over 8 years (it borders mine) and his dogs are a nuisance. I have heard him say exactly the same things about why he can’t take care of his property. He has money to buy beer and cigarettes, but not to haul his washing machine and car on blocks from from the driveway to the dump. He brags about how he lives off of a false disability claim. I would not dream of asking him if he would like my help. I have another neighbor who is 97 years old whose yard is beautiful. I underestimate the level of trashiness in my own yard; seeing it every day tends to blind you to it.
And there certainly are potential red flags in what he wrote. Obviously, we don’t know him, but according to what he said, he left his big ass pile of leaves in the space between the sidewalk and the street. Why on earth did you leave it in the space between the sidewalk and the street? Could you have possibly picked a more prominent place to leave them? “Yes right now it’s ugly, but I picked them up in previous years, I’m going to pick them up this year. It takes me a while, but I’ll get it done.” “I’m not going to leave my leaves where they are forever. I’ll get them cleaned up, they have 3 years of history to look at. Do I do it all in one day, no. But they get done.” How long do they stay sitting there? You state yourself that it’s ugly. It takes no more than 20 minutes to bag them up. You chose to wait to dispose of them, and by then, you’ll probably need to do it again, and the leaves are never done, they’re either waiting to be raked or waiting to be cleaned up from the planting strip/parking strip. You tried to treat weeds but “it didn’t work out too well.” For the last two years. Hmm. How bad does it look? It’s really not difficult to maintain a reasonable level of order. Whether you have a touchy back and a bad foot, or not, certain levels of order still have to be maintained if you’re going to own a home. Like I said, my 97-year-old neighbor can take care of it. I can let my yard go for a long while, too, but I confine it to the rear where it isn’t an eyesore.
And what do you consider to be “reasonably well-behaved” dogs? Do they run loose in the yard, are they chained in the yard, are they indoors but barking furiously at everyone who walks by? Do you even know if they are annoying anyone? Why would you have brought it up if you didn’t suspect it was a problem? Maybe it’s a non-issue, but again, this is we all say about our dogs, whether they’re angels or demon dogs.