Was there an objective reality that existed whether or not we could ever observe it?
Yes.
When do political parties start being a bad idea?
When people start voting for the bad guys just because they are in a party with some good guys.
Why don't we want the government controlling the internet but we're okay with them controlling our education system?
There seems to be something inherently authoritarian about education, so the government fits the genre. Internet is supposed to be fun, so the government does not fit here.
Is a democracy possible in the information age? Or has social media and technology changed the way humans function in a "democracy" and policy hasn't caught up yet?
Depends on what you mean by "democracy". Counting votes is actually easier in the information age.
How many people do I admire that are actually miserable?
Probably more than you expect, because hiding the misery usually makes one more admirable.
Is there really a difference between a more-disciplined person and a less-disciplined person, or do they just experience their temptations in different ways?
I can be either kind depending on the situation; in my case one important difference is the emotional state. If I feel optimistic, it is easier to overcome temptations.
These responses are based on my experiences, not through concrete evidence.
When do political parties start being a bad idea?
When you put humans in them.
Why don't we want the government controlling the internet but we're okay with them controlling our education system?
I wouldn't say we're okay with it, we've reached a point of inertia I'd say.
Where do jokes come from?
The need to alleviate the burden of living.
Is there really a difference between a more-disciplined person and a less-disciplined person, or do they just experience their temptations in different ways?
Anything genetic aside, I'd say upbringing and mindset.
Why isn't anyone building something like the Statue of Liberty, The Eiffel Tower, or The Great Bridge anymore?
There exist other goals that achieve more utility for the respective agents that hold this kind of power?
How is it some things existed in the past but there's no record of them in the present (online)?
Things get lost in time. People have to look out for them and bring them to surface.
Why is there no Thesis on Life or an almanack that answers these questions?
I haven't found exactly one as you describe, but I'd say many of your subquestions are either complex problems found in books by themselvs, or can be described in little text in trying to give concrete (but not complete) advice.
For example (short answer, long answer)
Many of your questions here aren't easy to unpack. For myself, it feels constructive to use cognitive behavioral therapy techniques to get curious about my "instinctual" answers to these, and see if I want to replace these with better and more constructive answers. Currently going though books in this series.