There may be some advantage to getting T-Nuts into place under a clamp bolt from the top, but expanding on the modified carriage bolt concept, why not a full T-Bolt instead of T-Nut? Something nicely fitting with a full strength rectangular head, strong enough, and large enough to spread the load. There would never be any danger of a bolt from the top hitting the bottom of the T-slot, and jacking very breakable bits.
The notion is so obvious that I think such stuff would probably have been around since the beginning of threaded anythings.