When I got my 97 F250 HD with the desiel, the options were 355, 373, and 410. I went with the 355 and it was a mistake. I would either stick with the 410 or maybe get a 373.
With the 355, I had to be above 80 for it to run decently. Loaded, below 80 it would lose speed when on cruise control and going up hills. Above 80 (even *way* above 80) it would maintain speed on cruise going up almost anything.
Throwing a whole bunch of gearing at it might not make as much difference with the mileage as you think. I had friends with 410 rears that got better mileage than my 355! (They also drove a little slower, too)