Tom is the best expert ...

Assertion of a fact. Where there are agreed criteria then there's no need to hedge an statement.

Djokavic is the current number one male tennis player in the world

When criteria are less certain, or we ourselves are not sure of our facts, or we wish to be modest by appearing to be uncertain of our facts we may use I think

I think Djokavic is the best male tennis played of all time

I think that the population of the UK is 50 million (actually 65 million)

This formulation implies that we are open to correction and discussion

Adding would softens this further, emphasises that we are uncertain

I would think that the population of the UK is greater than 50 million

The I would have thought formulation is normally used in a context where some information has recently been given. Depending upon the context it may imply that we are actually contradicting the information, or that we are expressing surprised acceptance.

I think Tendulakar is the best batsman of all time

I would have thought Bradman had a better record

that was disagreeing, suggesting that by some criteria Bradman is better

The current UK population is 65 million

Oh, I would have thought it was only 50 million

but now I've changed my opinion (this implied but not said)

that was agreeing, I thought it was 50 million, but I accept your statement of 60 million is correct. We could just say

Oh, I thought it was only 50 million

With pretty much the same meaning, the slight difference being that the second case implies it was actively in my mind, whereas the would form could imply that I hadn't really formed a solid opinion until now, but I would probably have guessed 50 million.

As your comment indicates we are indeed into shades of meaning and idioms. In these cases the tone of voice will often differentiate the meaning.

I would have thought Bradman had a better record

Would probably said with a questioning or challenging tone and raised eyebrow.

Ironically, one of the things that makes learning English tense challenging is the fact we have fairly few forms. Also, the question "is this grammatical" is tough to answer for short utterances without context, as we can almost always come up with some scenario when a native speaker might say it and be understood by other native speakers without anyone noticing anything out of place. A better question is "Does this mean what I think it means" and "Is this what native speakers would say."

So with that in mind, let me actually answer the question you asked!

These two sentences are very similar, so it is not surprising that you would be confused. There is a subtle technical distinction, but the more important distinction is a difference in meaning, which I'll get to.

Is This Grammatical

"I'm sure that would happen"

Grammatically this is fine by itself. I would take it to mean someone has asked you what would happen given some specific circumstances, e.g.:

a. "If I ran naked down the street, would someone call the authorities?"

b. "I'm sure that would happen."

"I'm sure that will happen"

Again, grammatically this is fine by itself. To me the most obvious context would be someone is asking you about your prediction of future events. E.g.:

a. "If I run naked down the street, will I be arrested?"

b. "I'm sure that will happen."

Which Should I Use?

or, "What's the difference?"

Technical Difference

I intentionally chose two examples that are very close together to make a point about agreement, not so much between verbs but between speakers: in the first example, person A says "If I RAN down the street". That "ran" is expressing a hypothetical circumstance (I believe it's technically known as "conditional II" because it's using a past tense verb to indicate something counterfactual). So it is only natural that person B would reply treating it as a hypothetical circumstance, too. Person A didn't say he was going to do it, he just wondered what would happen if he did.

In the second example, person A says "If I RUN down the street". This could still be hypothetical; in fact it probably is, since people don't usually run naked down the street. But because it's being phrased as an action that the person is actually contemplating, it seems a little more natural for person B to respond with "will". But note: "I'm sure that would happen" would also be a perfectly appropriate response.

Semantic Difference

In all the examples I used, everyone is still talking about things that haven't happened. By definition, then, these are "imagined events or situations" like it says in your grammar book. The difference is really based on how definite or how likely the imagined events seem to the speakers. Someone who says "I will" is implying that their imagined event is going to become reality, in a way that someone who says "I would" is not.

If you have a more detailed context, we can probably give you more definite advice to distinguish between the two.

For further reading, please see https://en.wikipedia.org/wiki/English_conditional_sentences which discusses a LOT of different possible uses of conditional in English (with sentence patterns).