That's what usual QT says without assuming Bohmian trajectories on top of the usual QT formalism. So what's gained by dBB compared to the standard "shutup and calculate" interpretation?
ad 1) I don't know. It depends on what happened to the system during the measurement, i.e., on the specific apparatus you used to measure the observable.
ad 2) Do you have a specific example? I guess you refer to single particles. Then such an example was how to measure momentum of a particle. For simplicity let's assume we know which particle we have, i.e., its mass and electric charge. Then you can e.g., use a bubble chamber (it's just the most simple example that comes to my mind; nowadays one uses all kinds of electronics, but that doesn't matter for the principle argument) in a magnetic field. The particle leaves a track in the bubble chamber (why it does so was derived by Mott from quantum mechanics as early as 1929); then you can measure the curvature of the track, and with the given mass, charge, and the magnetic field strength you know which momentum the particle had when entering the bubble chamber. Of course, in a way you measured position and inferred from this the momentum of the particle. All this doesn't need any additions to standard "shutup-and-calculate" QT.