There's no easy way to relate a^2 + 60 and a + 2 as written, because they have no obvious relationship, so we'll need to manufacture one. You might notice if we multiply (a + 2)(a + 30), we'll get a^2 + 60 + something else. So that will relate the two expressions:
(a + 2)(a + 30) = a^2 + 60 + 32a
a^2 + 60 = (a + 2)(a + 30) - 32a
and now we can rephrase the question: for how many positive integers a is
\(\\
\frac{(a + 2)(a + 30) - 32a}{a + 2} = \frac{(a + 2)(a + 30)}{a + 2} - \frac{32a}{a + 2} = a + 30 - \frac{32a}{a + 2}\\
\)
an integer. And since a + 30 is clearly an integer, we just need to know how many legal values of a make 32a/(a + 2) into an integer.
Now a and a + 2 are either consecutive even or consecutive odd integers. If they are consecutive odd integers, their GCD is 1, and since 32 has no odd divisors, nothing could possibly cancel from the fraction 32a/(a + 2). So a must be even. If a is even, a and a + 2 have a GCD of 2. So we know the numerator of the fraction is divisible by 32*2 = 64 (the extra '2' because a is even) and as long as a + 2 is a divisor of 64, the fraction will be an integer. So a + 2 can be equal to 4, 8, 16, 32 or 64 (it can't be 2 or 1, because a must be positive), giving us five values of a. Notice that a + 2 can't be equal to 128, or 256, or any other higher power of 2, because a+2 and a have a GCD of 2, so in those cases, the numerator is only divisible by 64, and the 2's will not all cancel from the fraction. And if a + 2 had any prime divisor different from 2, that prime won't cancel from the fraction, because it won't cancel from 32, and the GCD of a and a+2 is 1. So the five values we found for a, namely 2, 6, 14, 30 and 62, are the only five possible values.
Seems too hard for the GMAT though.