1.) Yes, build up the automatic. Specifically, a shift kit (valve body rework or upgraded shift solenoids), stronger torque converter, and possibly a better set of clutch packs (at least the end clutch since it is notoriously weak).
2.) You would need a toggle to set the shift position sensor at the correct value. Cruise control will not work in neutral, which is what you hard-wire when you do the manual swap (at least this is how it is on my 8G).
3.) Learning how to keep your foot steady.
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