Easy way to upgrade OBD I to OBD II

95 Dakota should be a hydraulic controlled trans, and if this is the case your suggestion is probably a good one.
The electrical connector on the drivers side towards the rear of the trans main case will have three wires if it's a hydraulic controlled.
If this is done there will have to be some system for applying OD and lockup.
This can be shifted manually with a switch, by buying an aftermarket trans controller or building a hydraulic pressure switching system like I built for my Dart.

This would apply even if he went with an EFI system instead of a carb.
(I'm kinda thinking in Montreal the self learning EFI would be the ticket)

For this truck the transmission is the 46RH, which is indeed hydraulically actuated. I'd prefer to keep the EFI system if at all possible as it gets very cold here in the winter. I've been trying to call Edelbrock and other places but keep getting put on hold for long periods of time, so I'm already starting to question the level of support for a project of this nature.