'92 D150 rebuild

I have a '92 Dodge D150 pickup with the original 318 engine.  Frankly, that engine with 170,000+ miles isn't up to pulling what I need to pull anymore and I'm considering doing an upgrade to it.  I don't want to spend the money on a new pickup so I'm considering an engine swap.  I have a 440 out of a '68 Chrysler New Yorker that got wrecked a few years back.  That engine has 72,000 ORIGINAL miles on it - yeah, that was a heart-breaker, but that old beast probably saved our lives.  If we'd been driving a current tin-can mobile, we probably wouldn't be here today.  Anyway, I'm trying to determine what kind of pitfalls I'm facing with that kind of engine swap.  I have several questions that I want to research before I start this project.

Will a 727 transmission fit in place of the original A518 that is in there now?  I've seen some articles that indicate the A518 is beefier than the 727 case-wise and that makes me think the 727 will fit.  I may have to modify the length of the driveshaft, but that shouldn't be a major problem.

I don't know whether to go with a carbureted system or to put on a fuel injection system.  If I stick with the Carter AFB carburetor, how do I go about setting up the linkages and what about my O2 sensors for the catalytic?  What would be my best option there?

Any ideas folks?  I'd appreciate any feedback on this possible project.  

If you are changing to a big block, the 318's 518 won't fit. If you are doing this swap for towing, you don't usually tow in OD anyway, so I would suggest a 727.

Also, if you choose an EFI set up, that will require some involved tuning with a computer--are you up to it?

I would go with a carburetor, and use a universal throttle cable from Lokar, and a universal throttle bracket like the one's from Mancini Racing

As far as your O2, just hook it up to an aftermarket A/F gauge, and you can keep an eye on the fuel mix.  
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