I am quite certain this is not helpful, and only vaugely related to the original post... but I'll post in case someone may be amused! I just had a major move. This included not only personal goods but also my business of 1500 books and thousands and thousands of yards of quilting fabric - both of which are VERY HEAVY. With s-i-l and daughter helping we loaded a 24' moving van and drove over an hour to new house. Too late, too tired to unload we went to bed deciding to unload in the morning. I woke up early and took dogs out to tinkle, all was fine. I took them to corner and back... and our moving van was sunk through the driveway on rr wheel to center of wheel. S-i-l couldn't get it to back out. Stuck but good. Neighbor driving by (looky-loo from next street over) tried to pull us out with a woven towstrap - it snapped. He went home and got a towchain and yanked us out of there. I promised to mention Ford F250 everytime this episode comes up. It looked like a Chihauhau pulling a Mastiff by a leash... but it worked. Driveway is about 4" thick asphalt, clearly a DIY jobby. I'm trying make this the 'brief version' but gotta tell the rest: Within about an hour the city crew came by, claimed all responsibility for the hole (said storm drain was down there and it should have held a moving truck). Patched up hole nicely. 4 or 5 days later we had a substantial rain. Driveway collapsed, twice as big now, about 18" across, and same depth. Glad I wasn't parked there. City came, dug it out bigger (little front-end scooper machine) and patched with just gravel this time. Week goes by, another rain, driveway collapses even bigger, now I can hear running water in the hole. City crew arrives, not so cheerful now. Digs it out bigger, could drop a VW beetle in there comfortably. Now we see the problem. (my nose is usually in the house but I do have to monitor what is going on out there ya know) Years ago when storm drain was installed ends of 20" cement pipe did not meet... so they threw a scrap of thin galvanized and a big blob of concrete over A FIFTEEN INCH GAP! The galvanized was nearly gone from rusting away. They fixed it up with a slice of similar pipe and more blobs of concrete. I hope it holds. Doubt it can fall in quite so spectacularly again. Photos at 5:00. Kidding, don't know how to post the photos... but I got 'em! GH

Thanks all for commenting. Of course we know it's not about "fixing the crack", but more about garden whimsy and perhaps a little encouragement to look differently on whatever seeming defects come up like that wonderful admonition of making lemonade when life gives you lemons. Making the sign on the back of a large iron skillet that my friend passed along is taking more time than making the 'river'. IF it turns out okay I'll post a picture. Happy whimsical gardening!

The section between the sidewalk and street is called your driveway apron. That concrete section will need to be replaced completely with a new one poured without a dip and you can slope it so there is a small 1/2" lip above the street's asphalt pavement to prevent some water from entering from the street. Usually always, and sounds like your case, this is your property but is located in an easement. That means you are responsible, but as needed for any service work the city has the right to access this area. It seems being in South Florida and with the adjacent parkway (the grass portion) this will always have muddy standing water, so IMO the cost of a couple grand would be justified. I am surprised the city would allow you to pipe a drain from the edge of your apron and tie into the street catch basin; however, this probably would not work. For one, you would only have a drain on one side of the apron, because to have one on the other side means you'd have to run the pipe crossing below the apron. But mainly why you wouldn't do this is because the apron is most likely not sloped within the dip towards the sides for the water to flow to any proposed drains at the edge. And just to discount what either the city could have been alluding to or someone else will offer, a french drain is not the answer. That would be a below-ground pipe with holes, that if run parallel to the street, would collect water soaking in the ground from above. Your problem is not solely based on water entering from the street, your apron is collecting water coming down your driveway and also from the adjacent grade in the parkway which is higher. And FWIW this has nothing to do with the trees.

Yes, unless you can do it, youll need a painter to prep and repaint.