a few things:
The big digger machine is referred to as an "excavator" and it looks like, to me, from looking at the machine from the rear that it is of volvo manufacture (might be wrong...) This will help you when talking to the city and contractors, as they will be more likely to believe you know what your talking about, trees or otherwise, if you are using the correct terminology. not trying to be a snob, trying to help.
also, having worked in all over the country, including ohio, in the energy and utilities industry, there is no way that they utilities on the opposite side of the street will be impinged by the placement of a sidewalk. The underground utilities would have been placed at a minimum of 36 inches below grade for frost protection, but often this is extended to 42 to 48 inches below grade. The placement of the concrete of the sidewalk would be no more than 6 inches thick, unless the town wants to pay for lots of unnecessary concrete. Airport runways are only 14 inches thick, and they handle alot more than foot traffic.
The drains and gutters will be another problem altogether. It looks like, from your pics and description that the drains are to be installed parallel to the road, right next to your prized Oak. depending on the depth of the excavation at that point (my guess is between 1 and 3 feet depending on the lay of the land) you may be able to to convince the city to use the 8 (or 12?) inch duct (pipe) on either side of the CRZ, and then transition to several 2 inch HDPE (High Density Polyethelyne- semi-rigid black plastic ducting) ducts through the CRZ, which using gentle hand excavation, you can identify the major roots in the designated excavation area, and actually splay out and intertwine the 2" ducts THROUGH the roots of your tree, without having to make any cuts to the root system. On the far side of the CRZ, you would bring the 2 inch HDPE ducts back into the 8 (or 12?) inch duct with an adapter (your city PW department should be able to procure the stuff I'm talking about with relative ease) so that the city maintains the required volume of water flow for their drainage system, and your CRZ is relatively uncompromised.
to be clear: use 8 or 12 inch pipe on either side of the tree, using an adapter, transition to several 2" pipes (flexible 2" HDPE or similar) to work the drain system through the roots of the oak, and when passed the CRZ, bring the 2" pipes back into the 8 or 12" pipe on the other side. The city gets their project, and the tree should remain healthy.
I have used this technique, the splaying of small ducts, to move entire duct banks (48 qty 4" ducts) up and over river flumes, drainage, and existing utilities, with as little as 12 inches of cover to the road surface. It will work if you can sell the city on this idea.
You can stay on as a consultant to the project, to either facilitate or monitor the gentle hand excavation and identification of the major roots within the CRZ that stand in the path of the drainage project, to position the ducts through the root structure, and ensure that the backfilling and site remediation in the CRZ is done with the best interest of the Oak.
If the city doesn't warm up to the idea of moving the sidewalk to the other side the street, try and sell them on a wooden, elevated "boardwalk" style sidewalk over the CRZ, as someone had mentioned in an earlier post. If anything, it might bring some quaint charm to an otherwise ignored part of town, as you had mentioned.
I know from working with these people on a daily basis (in places like DC, Boston, New York, Tampa/St. Pete, etc...) that the pencil pushers and shiny white hardhat types can be hell to deal with. Try and be polite and professional, but firm. Try and help them help you. They get their project, and you can help save a tree.
Best of luck and good wishes.