Brandon - It sounds like you did not find the OD relay, correct? It's easy to find AFTER you remove the glovebox (6-8 screws). After the glovebox is out, look into the opening toward the driver's side, sort of under the radio bay. The relay will be clipped to the dash support frame. It pops right out of the clip. See the following thread for more help in locating the relay, a photo of the relay, and repair instructions:
http://www.brickboard.com/RWD/index.htm?id=328036&show_all=1
Other, less likely sources of the problem include the shifter-mounted switch (probably ok if the overdrive light goes on and off when the switch is cycled), the overdrive solenoid (wiring can become frayed), and just possibly, the kickdown cable (I had a sticking kickdown cable on a 244 that mimicked an intermittent relay).
When OD operation is intermittent, can you hear the relay clicking?
Regarding the other problems with the car, you are probably aware that pre-1988 240s had engine wiring harness reliability problems that cause electrical faults. The scope of your son's problems sounds suspiciously like a degrading harness. There are numerous archive posts on doing a replacement, and one brickboarder used to sell good used non-degradable harnesses at a very reasonable cost. Perhaps somebody will chime in with the name...
Good luck, and don't give up on the brick. Intermittent OD problems CAN be solved. I had an OD problem (late shifting) in our '92 244 that defied diagnosis and repair. Good switch, relay, solenoid, and KD cable. Did a tranny flush/fill and changed the filter. Removed the tranny and disassembled the valve body. Nothing! Finally replaced the tranny with one from a parts car, and now it runs like a top.
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'88 244GL, '89 244GL, '90 244DL, '91 244, '92 244
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