Quick update and I'll also try to get the truck on a lift to take some pics soon.
After losing reverse I took the tranny in to get looked at. I found a fellow owner (67 Burb) that rebuilds trannies at Aamco. 27 years of experience. Made the decision to rebuild based on the gunk in the oil pan (metal shavings, etc. ehhh), but didn't feel up to the task myself. Watched as he broke it down...definitely needed the rebuild. Prior rebuild had some non-matching parts. He did a great job on the rebuild. I decided to throw a shift kit on as well. All came with a 2 year warranty parts/labor.
Also had the steering box replaced because it was going bad. Replaced the front/rear bearings as well after noticing I could wiggle the tires while it was up on the lift.
The guys also fixed an exhaust leak coming from the header/engine block connection, and cut/stretched a hose that was cracked.
Last thing was replacing the distributor because the wires were corroded and began shorting each other.
Results:
- Transmission shifts AWESOME (including reverse)

I peeled out coming out of the parking lot

- All the excess play is gone from the steering and it doesn't sway at higher speeds thanks to the new bearings.
- No loud pops and no shorting out.
- Whole truck sound TONS better with the exhaust leak fixed and doesn't sound like it's going to blow up at 60 mph anymore.
- Emptied the wallet a little bit but big blue is running/driving better than ever.
Next up (I'll be doing this stuff myself):
- Finish up engine tune up. Spark plugs, wires, hoses, check gaskets, fix oil leak from valve cover, etc.
- Start body work (I start 30 days of leave tomorrow so I should have the time I need to get it done)
- Make final choice on paint color. Keeping it blue just don't know what shade.