Highly recommend sticking with fuel injection if at all possible. Much better fuel delivery and diagnostic capabilities. Don't know of any issues with the head, will likely have to change the intake manifold.
If you're really after turbos - the 300 is probably not the best candidate.
As to the tranny question - don't know for sure, but wouldn't think it would cause problems.
Good luck, and keep us posted on your progress.
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1989 F150 XLT standard-cab shortbed 4x4, 5.0L, AOD, 3.55 gears, manual hubs, 31x10.50 tires, 212K miles. Repainted Oct09.
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