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Are they just actually the same?

  1. I'm not sure how much the trip will cost, I should think $500 will be ample.

  2. I'm not sure how much the trip will cost, I think $500 will be ample.

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    If you were to omit the "I'm not sure how much the trip will cost" and let the second clause stand alone, "should" adds a bit more willingness or invitation to hear why they should think otherwise. Without the "should" qualifier, it might be easier to read the declarative statement as a more firm conclusion. But, 'should' is also a bit formal sounding - it is not common in everyday speech of a averagely educated person or character on screen. HOWEVER, with the first clause, it ONLY sounds formal and a bit snooty as the uncertainty was already established. – Tom22 Jun 8 '18 at 2:56
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In all honesty, there is no difference between the two. When both are said, they are interpreted the same. The same is presented in the following phrases:

Do you care to join me this afternoon?

Would you care to join me this afternoon?

Although, the slight difference between phrases in both your example and my example is one is interpreted more formal than the other in certain situations.

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