You might start with posting a sign, maybe use the street name in the title or something like that. I keep wanting to make one for my yard but don't seem to get around to it. I think the biggest problem is when plants are too tall or aggressive and too many different heights, so I'd try to select ones that don't get taller than one or two feet especially close to the road or street maybe some taller stuff toward the back but even so, I think I'd stay with shorter plants. Also, plant a lot of annuals like gaillardia & Helenium annum so its a solid mass of color all season and self sowing with a lot flowers instead of a lot of green. It might make it seem a shame and therefore harder to mow that down if its ever blooming and colorful. Keep it simple, lots of repeats of massed plants of the same type in groups or swaths if possible, it looks less weedy especially to an untrained eye. The more kept looking it is, the better it will be. Wild looking, but planned. Most warm season grasses can take a couple mowings but not more from what I have read. Little bluestem stays pretty short until late summer and if the soil and moisture conditions are right it will look well behaved. I'd stay away from Joe Pye weed and other tall stuff like that. There is a median up the street from me planted in natives, its almost OK but could use a bit of TLC and selective weeding. An afternoon would make a difference.

blue grama can take a regular shearing much more often than 2-3 times a summer. It is often sold either singularly or as a component of drought tolerant turf grass. Mowing, I have read, actually encourages tillering, so getting a regular haircut would make it grow bigger. We had some good, thick stands of blue grama growing along the road that I used to either mow or use a string trimmer on at least twice a month, it never showed any ill effects from it.

Buffalo grass is a rhizomatous species, often sold as the other component (or again, b itself) of drought tolerant turf grass. It too can take a cutting just fine.

Both these species are common to dominant in the mixed and short grass prairie. Both are designed to withstand heavy grazing by large herbivores, so, a good shearing wont bother them a bit.

Unfortunately, most forbs do not take the same kind of abuse in such stride. While some pruning can encourage new growth, and branching repeated low mowing will likely be a destriment. At best, it would force some of them to flower very low to the ground (think the dandelions in your yard after you mow over them a few times, they start setting flowers right at ground level rather then on tall stems). Depending on timing they would either not bloom or could be killed outright.

Right^. Further, the constant disturbance of short mowing will aid weed seed germination. This is a tough one-wish I had a better answer.