We study global well-posedness and finite time blow-up of solutions for a nonlinear one-dimensional transport equation with nonlocal velocity , ν > 0, and measure initial data. Such model arises in fluid mechanics in vortex-sheet problems and its nonlocal feature comes from the presence of a singular integral operator (Hilbert transform ) in the velocity field. In the viscous case ν > 0, we analytically obtain an explicit condition on the size of the initial data for the global well-posedness in the framework of pseudomeasure spaces. In fact, we can give the condition depending on the initial-mass and analyze how the flow evolves from singular measures. Also, we numerically study blow-up of concentration type and global diffusion-smooth behavior of solutions. We obtain numerics that indicate the threshold value 2π for the initial-data mass that decides between blow-up or global smoothness of solutions. Such value is the same obtained for regular initial-data and by means of entropy methods. Thus, it seems to be intrinsic to the nonlocal PDE and independent of a particular framework, approach and initial-data regularity. The inviscid case ν = 0 is remarkable: simulations for model , evidence that the solution presents blow-up of concentration type with mass-preserving, while an attenuation effect is observed for the model with opposite sign in the nonlinearity , for any nontrivial (positive) measure as initial data.