I did exactly that earlier this year and it's worth every minute of the time to convert to an automatic, especially if you enjoy doing tougher trails. I did a trail last year where with my 5-speed and 4.88 gears, I couldn't make it up three rock (dry) waterfalls and had to be winched up all three. This year, I did the same trail after completing the conversion to an automatic and needed no winching up the exact same three desert rock water falls. That is due to the added torque and the torque converter you get with an automatic.
You could do the swap in a long weekend if you have all the parts. If Giancarlo lives close enough, go for it. The transmission is a 32RH which is what is in GIancarlo's '97, it bolts right up. You swap your flywheel for his flex plate, pull your pilot bearing, and bolt it up. You would need a different computer for a '02 TJ with a 4.0L engine and automatic, yours wouldn't work and neither would Giancarlos because his is a '97 which has different programming. The wiring for the torque converter is already there, no wiring needs to be added or changed.
It's a great swap, I'm digging my automatic.