Many transportation agencies are experimenting with innovative contractual arrangements for the procurement of construction, maintenance and operation of roads. They are changing from traditional contracts that prescribe the kind of work that need to be done in a specific section of the network, to more flexible contracts, increasing the contractors freedom to its maximum level, where the contractor itself decide which section, when and what kind of work he will perform, with the only condition of keeping a certain level of performance for a whole road network. Advanced computer models have been developed that estimate what would be the resulting road condition for given investment decisions and maintenance actions. Nevertheless it remains uncertain if contractors are given the freedom: What trade-offs would they make? Will road quality decrease? Will road agencies be able to monitor or control contractors? Before all these choices and freedom are transferred to the private sector, it is urgent to develop a clear view of the most important trade-offs that are now already made by the public authority. In order to contribute to the building of this understanding this paper explores the issue of road condition and some of the most the relevant and conflicting aspects of it.