I am not sure how to assess myself in terms of being an optimist, realist or pessimist. Do you assess yourself through your own observations of yourself over time, or asking other people, or some more reliable psychological tests, or anything else?
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How to assess yourself or others in this regard is a good question. I haven't given much thought as to how to do it best, mostly I just "do it" :-)
When I think about it, I've probably used a few methods.
First, as an "absolute method", I try to assess my immediate or "gut feeling" versus my rational assessment about future outcomes.
The second method, which is more of a relative measure of my optimism/pessimism compared to other people, is to observe how different people assess future outcomes of the same events. Obviously rational thought plays a role here as well, perturbing the results, but when the observations are performed over a large number of events, the mistaken rationales will start to average out to the point where you can see relative bias in one direction or another emerge.
And finally I've used two of the methods you suggested: observing myself over time and asking others to assess me. Truthfully though, I tend to trust my own assessment on the topic versus most other people's opinions, since they don't typically have access to the internal thoughts that lead to my expectations. So unless someone has been able to observe me for a long time or I've shared with them my thoughts that lead to my expectations, it can be difficult for them to accurately assess whether I'm a pessimist or an optimist (basically the same problem I mentioned in the relative measurement method: rationales perturb the result).
I've never taken a psychological test to try to measure something like this. I guess it might be worth a try, but I think I can probably "guess" the thrust of the questions, so I think such tests would likely not be very helpful for me. At least, this has been my experience in the past with the few other psychological tests I've taken: I feel I can guide them towards whatever answer I feel like at the moment.