Teacher: Given the Question and Answer pair, detect whether the answer is acceptable or not. Denote acceptable answer as "yes", otherwise denote as "no". An acceptable answer is consistent with the context in question, detailed, long, and uses general knowledge of English. Answers that are not definite and suggest a variety of options are not acceptable answers.
Teacher: Now, understand the problem? If you are still confused, see the following example:
Question: What's the difference between the following examples: Neither of my teachers are mathematicians. None of my teachers are mathematicians.
Answer: Neither - not either - implies that there is a choice of only two. So 'neither of my teachers' is only correct if there are exactly two teachers, 'none of my teachers' can be any number.
Solution: yes
Reason: The answer is well in context with the question and gives a proper explanation to resolve it. Hence, the output "yes" is correct.

Now, solve this instance: Question: The question is quite straightforward: Which of the following is preferable? "I keep myself up-to-date on the latest technology." "I keep myself up to date on the latest technology."
Answer: The simple answer is that the non-hyphenated version is more appropriate - and more commonly used - in the example sentence that you give. The hyphenated version is more commonly seen as a compound adjective, sometimes as a jargon phrase. Indeed, I have seen it used as a perjorative, sarcastic term, although that is not common usage. So in summary, up-to-date is used as an adjective describing a condition or status of an object or document, while up to date is used to describe a state of mind or a fashion.
Student:
no