Very Interesting matchup
Kamui should suffice as a hard-counter to Glamour World, so Obito's defence shouldn't be too much of a factor and his attack output would be put under the lens realistically.
While his Shuriken and Stakes probably wouldn't be too effective as they're more suited for bigger/multiple targets. His Fire-style (
which comes courtesy of him being unmasked) could prove to be extremely potent as it's completely indentical to Madara's Fire-style in terms of size and AP, and considering Obito's AP advantage juxtaposed with Dorothy's durability then this would likely deal pretty substantial damage.
With that said, it's unlikely that this would be able to 1-shot and as a result it probably won't result in a win by itself.
Obito's biggest win-condition here would actually be the human path of the Rinnegan. By grabbing onto his opponent he can effectively just rip out the soul of whoever he gets a hold of (not having to worry about durability).
This would actually be somewhat in-character for Obito to do aswell as he originally wanted to use the human path for interregation early during the 4th war and charging to grab someone before subsequently killing them was done during the fight against Konan.
Although Obito has to expend an extremely big amount of chakra to use the Rinnegan, he was still capable of using it to create his own version of
the 6 paths of Pain while simultaneously supressing the Bijuu, so choosing to use the Rinnegan shouldn't be too much of a detriment.
As a result, Obito does have a good number of win-conditions present, and taking Kamui into consideration makes it very plausible for him to fulfill those conditions while countering almost anything that could go against him.