Getting to a round of changes to the team optimizer is on the list, but we have a few other things stacked up.
The main thing is our new "version 3" gearing strategies, which will be much better at choosing legendary items and adapting to your chosen talents.
As for "comparing to random gear", I can't reproduce this. I would need steps to reproduce in order to debug it further.
Usually this happens when some information is out of date for a character... the team optimizer is currently quite sensitive to every player on your team keeping things very up to date. That is one of the things we want to think about for the next version of the team optimizer -- making it a bit easier to use.
For now, most problems can be fixed by ensuring that every person has the addon, every person has every spec updated and configured as desired, and every person has a well-maintained public profile. It really is a tool designed for an entire team that wants to do data-driven optimization.