FWIW, you should make sure whatever connector you use is designed for “blind mating”. Those are connectors with tapered surfaces, extra alignment pins, or other features designed to make the connector tolerant of misalignment, so that it basically self-aligns as it gets inserted. Remember also that some part of the design has to have the freedom of movement to overcome the alignment tolerances in the individual assemblies. So if you’re using connectors that require x misalignment maximum, and your board assembly allows x misalignment on both sides, you’ve got up to 2x total misalignment. If your mounting holes have 2x or more of freedom of movement, then you can still mate, but if not, you’ll run into trouble. (Some blind mating connectors actually have floating contacts and inserts, so that the connector itself can move to accommodate tolerances.)