Hi Erin,
As a TS-lover (and a bigtime Roe user), I would suggest the Chindy 88 over the 101. This is because with clever use of the spacers you can use it for TS and Hybrid. The 101 is a touch wide for true TS.
The same options are possible with the truck I switched to last month...The mighty Dragonslayer 90mm. An awesome truck IMHO.

If you go for the DS90, you can run it as a front truck, a rear with de-wedging and you can do the same on your Unlimited with the spacers on the insides!
As for bushings, white Khiros work really well in the front and top rear (or a Tracker blue) with a green stim on the bottom...
You need to experiment for yourself, but I find my board runs a tighter line to the cones when my front truck/wheel combo is slightly wider than the rear. It seems to follow more like a car with the rear turning less and therefore providing more grip. If you are keen to stick with the Tracker 106mm, then the 101 Indy Offset would work, but if you want to get into 5 1/2ft tight etc, you may have to go narrower...
Hope that this helps,
Martin.
ps. In the 2nd pic, my Unlimited has a 110mm Gus truck- very underrated inexpensive front truck that turns more smoothly than an Indy and has won a World TS title with Michael Stride, a TS and a Slalom title with Maurus Strobel! The 3rd board has Indy/Indy Offset combo for GS/SG.