Apologies to davance for the worst case scenario I am going to present.
Having done this quite a few times, I highly recommend not writing a single line of code before you read not only the specification, but any kind of email from the JSR expert group.
JSR specifications are usually ambiguous and can be interpreted in several different ways. After going through this in a very methodical way, you will be able to ask the appropriate questions to the expert group soon enough before it is rejected and becomes unresponsive, I hope.
TCK is usually a set of tests that do not guarantee that your implementation will work even remotely, but simply says that you are a legal implementation of the specifications.
TCK is usually too expensive to buy an individual.
Abundantly, the way JSR is implemented will depend on which operating system and which virtual machine you are targeting. The nicer JSRs are usually those that can be implemented in pure Java.
Good luck
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