Next day we got on to more intimate subjects and I began to learn something of his life. He was now nearer fifty than forty years of age, though I should have thought him younger.
I had been surprised on the evening of our first meeting to discover the nature of his work. He was engaged in selling sewing machines on commission to Indian storekeepers up and down the East African coast. It was clearly not the job for which his age and education should have fitted him. Later I learned the explanation.
Source: Too Much Tolerance, by Evelyn Waugh
I guess in the first example should have thought should be equivalent to would have thought, but I was wondering if "thought" or "had thought" could be used instead without changing the intended meaning.
As for the second example, I would think "should fit" should be used instead because obviously he was still engaged in his sales job at the narrative time. Does this should have done construction here imply an unfulfilled expectation?
If I cast this example into the present, will it be "It is clearly not the job for which his age and education should fit him."?
Answer
I can only read these passages with a somewhat colonial-era mindset - that is, the language seems to be from a few decades ago, or maybe present-day Britain (I'm not sure, I wasn't there long enough last time).
In any case:
He was now nearer fifty than forty years of age, though I should have thought him younger.
In this case, should is being used to express that the thought "he is younger than 50" was the more appropriate thought.
As for whether or not you can remove should and have and keep the meaning: should usually reduces certainty - conveys conditionality upon another circumstance.
However, in this case it appears to express propriety, which is a meaning that you're unlikely to glean from the text if you're not a native speaker. I would say that today, you could remove should and have the same meaning, but in the register of the pre-1960s, I'm not sure that's the case (and I believe that that's off-topic here).
For removing have, this would be a distinction between using the simple past and the pluperfect, where the simple past merely refers to an action completed (sometimes habitually) in the past.
The pluperfect refers to an action completed in the past, at a time earlier than the time currently being projected.
That being the case, I think that using the simple past instead, in this context, would not change the meaning.
It was clearly not the job for which his age and education should have fitted him.
With regards to should, I would assert that it's again about propriety, rather than desire, as in the first example - they're both closer to expectation.
These days, I think we would say suited rather than fitted, although I understand the meaning.
I don't think using "fits" for a job is as idiomatic today, as "suits" is.
However, if the distribution and usage is the same, I would guess that your proposed sentence would be acceptable. It's a bit of an edge case, though.
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