I have done that in the past, and it never made me sleep all warm and fuzzy, although you're right. There are solutions. Too complicated, and without a trans temp gauge, I was always afraid of one of those bypasses failing and toasting things.
I also can't imagine that buying and plumbing all that would be cheaper than just getting a radiator with the extra circuit and doing it "right."
You'll get a lot of other opinions on putting an external cooler before or after the radiator. I always say before. For the same reasons I mentioned before, if you put it after, you will almost certainly overcool the fluid. Putting it before means you either undercool (too small) but you're still helping the radiator shed heat, or overcool (too big) but the radiator can return it to the proper temp. Putting it after means you'll have correct temp fluid leaving the radiator 95% of the time, and then overcooling it to send it back to the transmission.