Yes, a properly done pressure test will tell you "where" the leak is.
The four main sources for water intrusion into the lower unit would be (in no particular order):
the seals on the fill/vent/level plugs/screws (many models only have fill and vent plugs)
the big o-ring (seal) on the bearing carrier
the propshaft seal
the waterpump base/seal
A proper test would involve applying air pressure to the lower unit (normally pumped in through the oil fill with a pressure gauge connected to the oil vent). The propshaft, driveshaft and shift shaft are then rotated or wiggled and if the air pressure drops then you move onto the next step.
The unit is then submerged in water, where you can see where air is escaping - thus determining which seal has failed.
Many shops will charge about 1/2 hours labour to do the test. If you have a compressor (need 10-15 psi in the lower unit) and a pressure gauge you could do it yourself at home....