If you can't answer these questions, then there is no point proceeding with other questions about specific workouts, race equipment, race schedule, strategies, coaching or anything else you're trying to decide on.
Why? Because the answer which makes the most sense should be the one which most closely matches the goals you have set. For example, "Do I need to get a Zipp 808 and disc wheel for a few thousand dollars for my upcoming half-ironman?" The answer will greatly depend on if your goal is to finish with a smile on your face, move up your age-group, go for a Clearwater spot, or even win your age-group. It makes no sense to spend thousands on Zipp wheelsets if you're just wanting to finish with a smile.
Whether you should do a race when battling a slight injury, continue with a workout when clearly tired, or invest in coaching, massage, power meters, Garmins, etc, all depend on the answers to the questions stated in the first paragraph.
I get people who ask me what I think about all of these things and situations, and 100% of the time my answer is, "It depends on your goals". Some people quickly and easily respond to me with clear and concise goals, but others stare at me with a look of bewilderment. If you tell me your goals, I can give you some advice that will probably help. If you have no goals, then I have no idea if the advice I give could help or hurt.
Make sure the first decision you make for your season is to set the goals, and then prioritize them. Write them down, so you can easily refer back to them, even if that means writing them on a poster on the wall. Anytime you have a question, go back and see which decisions will be in support of those goals, and are necessary for achieving them. Your goals are the standard for which all decisions should be judged.
So if you have a question you want help with, I'm happy to provide advice. However, you need to provide me with the knowledge of what your goals are. Otherwise, I'm not giving you advice, I'm just giving you words.