First things first here!
If you have the domain parked make sure none of the adverts on the parked pages links to their company, a company selling their products, or indeed to any of their competitors! (Same goes for adverts on a developed website if you have developed it.) It is better to be safe than sorry.
Now as far as your 2nd question goes it is up in the air (but by doing the above you increase your chances of success). It really decides on the following:
1. The word in question.
2. It's degree of ubiquity of use as a TM as regards common usage.
3. How good their lawyers are.
4. How good your lawyers are.
5. Have you a history as regards TM domains
6. The knowledge of the relevant law held by the judge or adjudicator.
7. What side of the bed the judge/adjudicator got out of.
As regards your first question it depends which route they would like to take. To go the UDRP route will cost them a $1,000 to start with, and that is without the costs involved of hiring a lawyer. To go the court route could cost them conciderably more. But at what point it becomes worthwhile them fighting you for the name is something that only they know.
It may be worth while dropping John Berryhill an email to get his take on this.
Others here may be able to flesh out more on your questions, but here is wishing you good luck and hope you get a decent price for your domain.
Edit addition.
As quickly as possible make up a site around the meaning of the word with no reference to the company or clothing.