Upgrading Items

@GridironGuy88 I did a few experiments. Unfortunately my Servo is not skilled enough to test with having him upgrade, and none of my speakers needed repair. I found a few things to be factors, and a couple surprised me in a way that may or may not be part of the issue you're having in regards to Servo:

• He could not order parts for upgrades on the computer. This may or may not have been a Servo-specific thing, or due to him only having handiness of 1. However, I was able to drag parts from my other Sim's inventory into Servo's inventory. (But upgrading the speaker apparently took a higher handiness anyway), so that made no difference for my testing purposes.
• Servo had the option to turn music off and on on the outdoor speaker, but the animation of using the remote didn't happen, though it did happen inside when he turned it off and on.
• Servo had the option to dance at the outdoor speaker, however he only gave the 'can't route' bubble animation when asked to. When asked to listen to the music at the outside speaker he also did not do the 'bouncing head' animation:
  
• When a wall speaker was inside, Servo did not have the the option to dance at the speaker, but that may have been because that area was a bit less open?
  When asked to listen to the music at the inside speaker he did do the 'bouncing head' animation, and when he turned the music on/off at this speaker he did have the 'use the remote' animation also:
  
• I checked at the vintage stereo (indoors) and he did have the dance option there and danced successfully:
  
• As an aside, I tested on a broken dishwasher and Servo was able to do the repair on it when I moved it into the yard.

So, though this was not a thorough test of all potential factors, I think this may indicate, combined with your results, that Servo may not be properly interacting with wall speakers that are placed outside.