Todd, if you do something, are you going to do it yourself? We can't give a bolt by bolt description.
You asked about the "advantages over what you have. Other than the fact it's overdrive and automatic". If you don't see any, then it's none, besides those two.
In general: You remove the trans and bell housing. Remove old trans cross member. Remove anything that is for the manual trans. Install a flexplate, torque converter and the automatic transmission. Provide a cross member for the transmission tail. Have your drive shaft modified to correct length with proper slip yoke for Auto trans.
Provide a vacuum source to A/T. Provide a radiator for A/T with oil line ports. Install Lokar nostalgic shifter on trans. Remove clutch pedal if you want. You probably want the non-computer version of whatever OD auto trans you decide on. It's not very hard to do. The A/T will bolt right up.
look at Classic Truck PN's 79-507 and 79-235 to see what an aftermarket A/T cross member looks like and pad. It's all just searching, reading, dinker, tinker, measure, and don't sweat the small stuff.
"Difficulty" level of the swap is subjective. Depending on your level and experience and if you have a jack and some jack stands. For myself, I know it's a bit of grunting but it is not high tech because all the parts for SBC are readily available. It's out with the old and in with the new. You get all the parts taken off and then you buy what fits per above. You can handle it if you have a good level place to work and a buddy or two. Find a good old boy who is a retired tranny builder to build the 700r4. It does not take a fancy TCI or transmission shop to build one for a 283.
You want a 1987-1992 700r4 or 4L60 (same thing).The 4L60E is the electronic controlled.
