Devices and systems for injecting fluids, such as anesthetics, to or near nerve tissue or other targeted anatomical location are disclosed herein. A conduit is generally configured to place the fluid delivery module in fluid communication with a needle that is configured to be inserted into the patient's anatomy. One or more medicaments (e.g., anesthetics) and/or other materials contained within containers (e.g., vials) that are secured to the injection system can be selectively delivered into an anatomy through the needle. Nerve stimulation and/or imaging technologies (e.g., ultrasound) can be used to locate a targeted anatomical location. Aspiration can be used to confirm needle location. An overlay on the imaging display can include, in addition to real-time imaging data, data and other information relating to back pressure at or near the needle tip, volumes or other amounts of fluids delivered by and remaining within the system, stimulation level and/or the like.