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Nate a couple of thoughts.

First on the old truck type 5-speeds most were not overdrive. You will want to check and see which one you actually have.

Second I've toyed with the Diesel conversion idea a few times too, and keep deciding to stay with my gasoline motors.

Part of that is just that I like the rumble of a big V-8 while the sound of a Diesel doesn't move me. But part of it is economics. The conclusion I've reached is that you have to drive a lot of miles before doubling your fuel economy saves enough money to pay for the convesion.

I just don't drive my bigger rigs that much.

Third, if a 409 was in there, a 454-502-572 will go back in pretty easy. I have one good running 454 I got for free (in a junk truck). A crate 572 can be had for about $15,000. Somewhere between those two numbers you can probably find a good motor that fits your budget.

Buy a used big block and for far less money than a Diesel conversion you can be running that truck around pretty fast.

It may not pull as hard and will likely use a lot more fuel, but you can buy a lot of gasoline for five to ten thousand dollars, plus you buy as you need it and don't pay interest or loose investment income on the capital investment the Diesel conversion could require.

If you have a passion for Diesel then I'm sure its worth it. But otherwise consider the economics carefully.