A very interesting question... Congratulations, @pyler!
I am closely connected with the Miller theorem and, a few years ago, I spent a lot of efforts to reveal the idea on which it is based. In 2011, I created and fully wrote the Wikipedia page about the theorem. More precisely speaking, this page was dedicated not so much to the very theorem, but rather to the extremely useful applications of this Miller arrangement (a voltage source connected in series to an impedance element) in analog circuitry.
Besides its use as a "mathematical tool" (as alex.forencich said), it is an extremely powerful tool for creating virtual elements; I have dedicated a special question about it in ResearchGate - How do we create virtual electrical elements in electronics? The recipy is extremely simple - insert an additional voltage source in series with the impedance and vary its voltage proportionally to the input voltage. Thus you can decrease up to zero and even invert... or increase up to infinty and invert again the impedance... Now about the concrete question; here are my considerations.
My note to alex.forencich is that it is not mandatory the circuit to be grounded; it is enough just to close the loop. But if we ground the sources, we will more easily see that the second source, compared with the first, has an opposite polarity (+) with respect to ground. Тhis requires the coefficient K in the expression to be negative and then the denominator is K = 2.5 instead of -0.5; just to correct that the theorem states that Z1 = Z/(1 - K).
So, the new resistance is Z1 = 100/2.5 = 40 ohm... it is not negative... it is just the (2.5 times) decreased old resistance Z. Now, the most interesting part of my comment - I assert that we cannot obtain a negative resistance with this simple Miller arrangement... and I will try to explain why.
In this arrangement, the two sources are connected in series and in the same direction when travelling the loop (+ -, + -). So, the second source V2 increases the overall voltage (2 + 3 = 5 V vs the initial 2 V) and thus increases 2.5 times the common current (I = 5/100 = 50 mA vs the initial 2/100 - 20 mA). As a result, the new input resistance is 2/50 = 40 ohm; it is simply decreased. We can decrease it even more by increasing further V2 but we can reach only zero... we cannot go beyond this point... we cannot invert this resistance to obtain a negative resistance.
To invert the resistance, we have to invert the overal voltage across the network Z - V2 (i.e., the voltage across the new virtual "resistor" Z1). But we cannot invert this voltage since this network is connected to an ideal voltage source that defines the voltage. To do it, we have to connect another resistor in series to the input voltage source. Then the current will keep its old direction but the voltage across the network will change its polarity to the opposite... and the ratio V/I will become negative. This kind of circuits are named voltage inversion negative impedance converters (VNIC). See my Wikibooks stories about the S-shaped negative resistance and the operation of VNIC.