I've lived in three major cities, always near interstates and bypasses. Milwaukee's I-94, Kansas City's I-35, and Jacksonville's I-95. The 894, 235, and 295 circled these cities, making travel faster. However, the directional naming of these roads often left folks from out of town confused. Honestly, even people who live in the locales probably get confused. But there's a simple fix that can apply to all interstate bypasses that go around a city, and it makes so much sense that I'm sure it's been proposed before. I have to wonder why this naming has never been adopted.
My initial idea was to identify clockwise or counterclockwise. I think it would work after some time of people imagining themselves looking down on a map from above. For example, the 295 counterclockwise from the airport in Jacksonville would indicate you are going west and then south. These could also be called inside and outside, since clockwise would always be on the inside while counterclockwise would always be on the outside. 50 years ago or even 20 years ago, this naming scheme would have saved countless headaches and probably some lives. But most of us no longer think of a city from a north-up map or clocks with dials, and the time that people might need in order to imagine where they are in relation to being clockwise might prove excessive.
The key is identifying initial actual direction AND future directions. By adding three directions to the name of the bypass at any given point, drivers will be able to know precisely where they are AND where they are headed (without thinking too hard). The same 295 westbound (counterclockwise) near Jacksonville's airport as above would be called 295 wse. In fact, the current naming calls one direction northbound and the other southbound near the airport (north side of town) and near Orange Park (south end of Jax). But both roads really go south from the airport and north from Orange Park. Circular roads need different naming than straight roads. So from Orange Park, you'd take 295 enw towards the Beaches or wne towards Baldwin. Along the 10 on the west side, you might take 295 nes towards the airport and 295 sen towards Orange Park. But on Atlantic Avenue further east, you'd take 295 nws towards the airport and 295 swn towards Orange Park. If you know generally where you are in relation to the center of the circle, this naming scheme is perfect. You'd still need to see signs for Daytona Beach or Savannah in order to understand which road you'd need to continue on the 95, but for people trying to use the bypass for local navigation the multi-directional system is best.
In a perfect world with extra-large signs, I suppose you could combine both of my ideas, so the 295 crossing the Dames Point towards the airport in Jacksonville would be 295 nws out. Taking it even further, you could add 95 intersection with a bold or capitalized letter, so 295 nWs indicates the 95 intersects with the 295 as it heads west. If you were getting on the same road at Main Street, it would be 295 WsE, but getting on at Duval Rd (on the other side of the 95 interchange) would be 295 wsE because the 295 does not intersect with the 95 in this direction until Mandarin. I know, at some point maybe it's TMI, but the directional attributes could really be bolted on to existing signs, at least at decision-making points near ramps.
Even accidents should be reported more logically with my system. Instead of saying "accident w295 nb near Orange Park," you'd say "accident in295 wnE near Orange Park." That's the inside, clockwise road that heads west and then north but does not intersect the 95 until it heads back east. Knowing this information, a traveler could decide to take 95 north through downtown or go enW on the outside 295 to avoid the accident.
I'm sure that an idea like mine will probably never be implemented, especially with the prevalence of navigation devices, but I consider it a better system than currently exists, so it's just unfortunate I published the idea a few decades too late. Perhaps it can be used in naming the air roads for the flying cars we're all waiting to purchase.