Short answer, driving 60 ton MBTs down most modern highways will do minimal damage assuming the drivers are reasonably cautious and the roads were built to sustain heavy truck traffic. It will not make them impassable for trucks afterward, but locals may still ask for compensation due to damage.
Driving 20 – 30 vehicles down DRY gravel or dirt roads will likely not do too much damage assuming the roads are dry and foundation is stable. Crushing of culverts may occur. It will not likely have immediete effect on tactical vehicle traffic. It is very likely to have long term (how long term will be effected by amount of rain) effects on the road, as the water originally intended to go through the culvert washes out the road…
In many urban areas, tanks and larger APCs have serious challenges driving along roads without knocking into walls… This was fairly common in areas in Iraq were many of the secondary roads seemed like alleys with compound walls defining the roads. The walls would often get 'bumped' and collapse. In one case I saw a wall collapse just do to tanks and AAV 'rumbling' by. I'm certain no vehicle actually touched the wall, but the vibrations caused it's collapse. Rubble in the road obviously will effect movement of vehicles.
Wet dirt or gravel roads or roads that are built on/across sand, peat, marsh… are entirely different. You will likely end up with 'ruts' that make use of road difficult.
In a campaign game I'd tell the player that it units have identified issues with trafficability at X (or X, Y and Z locations) and he/she needs to assign an Engineer unit (Plt, Co, Bn?) for a certain number of days/turns to maintain the road or he loses 'road march' speed advantages, or ability to move supplies along that route… Same can/should be done with other key infrastructure (ports, airfields, dams…). Usually degradation of a road occurs over time and the player should get some warning before the effects slow/cripple his logistics.
You might also make him decide wheter he accepts a slow down in traffic, while engineers maintain the road, vice a loss of use of the road in 2d6 days…