From the perspective of quantum thermodynamics, realisable measurements cost work and result in measurement devices that are not perfectly correlated with the measured systems. We investigate the consequences for the estimation of work in non-equilibrium processes and for the fundamental structure of the work fluctuations when one assumes that the measurements are non-ideal. We show that obtaining work estimates and their statistical moments at finite work cost implies an imperfection of the estimates themselves: more accurate estimates incur higher costs. Our results provide a qualitative relation between the cost of obtaining information about work and the trustworthiness of this information. Moreover, we show that Jarzynskis equality can be maintained exactly at the expense of a correction that depends only on the systems energy scale, while the more general fluctuation relation due to Crooks no longer holds when the cost of the work estimation procedure is finite. We show that precise links between dissipation and irreversibility can be extended to the non-ideal situation.