Thanks to people on here I heard about Tom Zont and his shop awhile back. At the time however, their shop was located at least one time zone away from Chicago, and I was satisfied to have my dirtbikes held together with zipties and HDTony's good intentions.
Life afforded me a house in the middle of nowhere, and a nicer dirtbike. As it turns out, it was also close enough to the TZR shop that the trip didn't require a passport and a change of underpants (I keep a change with me regardless).
Took the new-to-me bike in for some refresh and maintenance last weekend, and have been blown away by the level of customer service and attention they have given me since. Blown away.
For those that don't know, I share Bug's mechanical impotence. I freely admit that I haven't mastered the concept of "righty tighty" and I know my place in the garage is close to the beer, and far away from the wrenches.
Much to my surprise, Scott Zont didn't laugh me out of his shop. Instead he took the time to translate things to me in a way that I could understand, and went above and beyond with little tweaks and extra (minor) repairs to make sure I spend my season riding instead of pushing.
Having worked at a bike shop (albeit a shitty one) and expecting to be miserable whenever I take something to a mechanic - I was pleasantly surprised to be treated like a customer from start to finish. Moreover, I feel as though the work they did was top shelf, the pricing was upfront and fair, and would highly recommend them to anyone looking for professional dirtbike services near LITH.
Thanks to all the guys here for the great recommendation. I will definitely be back.