I doubt that. First you have to get by a Taney court. Second you need a offence to litigate. Third you need a open court in the federal district where the offense happened. Then there is the political question issue that a federal court might not rule on.
Everything you mention is easily handled in December of 1860.
- Taney (according to what he leaked and what was in his files) wanted to allow the secession
- A test case is easy to create. Example: One state (say South Carolina) declares secession and an import tariff. Another has someone import some goods into SC and objects that South Carolina cannot impose that Tax according to the US Constitution. If that isn't to your liking, pick something else that works better.
- File your case with a judge you know. Easily done and men available, including a Supreme Court Justice or two down at the circuit level (as Taney did in Ex Parte Merryman a few months later) in the South. You can get a preliminary ruling quickly.
- In 1860 Andrew G. Magrath would have been the District Judge for South Carolina. You'd need to get him to hold off on his resignation (he'd submitted it after Lincoln was elected and become the South Carolina Secretary of State; Davis made him a Confederate District Judge in 1861; Governor of South Carolina when the war ended) if you wanted to use him, but with a little planning that would not be a problem: just stay on as a US Judge a little longer. It is pretty clear which way he would have ruled, IMHO. (South Carolina had 2 Districts but only 1 Judge until 1901.)
- Assuming the Circuits were the same then-as-now, South Carolina would have been part of the Fourth Circuit, which also included Maryland, so Taney would have no problem filing. However, no one seems exactly how Taney was acting when he filed the Ex parte Merryman order with the Maryland Court and some think he was doing it under a more general authority from the original 1789 Judicial Act. Maybe any Justice could have filed it, which gives us Campbell of Alabama.
- If the court agrees to hear your case, fine: you get a definitive answer.
- If the court refuse your appeal, that's an answer as well
- If the court declares it a political matter and punts it over to Congress, that's still another answer. Now you can go to Congress and slug it out there (easier to do if you keep your representation in the House and Senate until it is resolved).