I'm gonna leave off the Or Y < 5 part of the expression for this post as uninteresting, and limit myself to the X > (-2 And X < 2) side of the expression.
I haven't done much VB over the last several years, so I started out with some digging into Operator Precedence rules in VB, to be sure I have things right. I found definitive info on VBA and VB.Net, and some MSDN stuff that might have been VB6 but could also have been the 2013 version of VB.Net. All of them, though, gave the < and > comparison operators higher precedence over the And operator, regardless of whether you see And as logical or bitwise.
With that info, and also knowing that we must look inside parentheses first, I'm now confident the very first part of the expression to be evaluated is X < 2 (rather than -2 And X). Further, we know this will produce a Boolean result, and this Boolean result must be then converted to an Integer to do a bitwise (not logical) And with -2. That result (I'll call it n), which is still an Integer, can at last be compared to see if X > n, which will yield the final result of the expression as a Boolean.
I did some more digging and found this Stack Overflow answer about converting VB Booleans to Integers. While not definitive documentation, I was once privileged to meet the author (Hi @JaredPar) and know he worked on the VB compiler team at Microsoft, so he should know what he's talking about. It indicates that VB Boolean True has the surprising value of -1 as an integer! False becomes the more-normal 0.
At this point we need to talk about the binary representation of negative numbers. Using this reference as a guide (I do vaguely remember learning about this in college, but it's not the kind of thing I need every day), I'm going to provide a conversion table for integers from -3 to +3 in an imaginary integer size of only 4 bits (short version: invert the bit pattern and add one to get the negative representation):
-3 1101
-2 1110
-1 1111 --this helps explain **why** -1 was used for True
0 0000
1 0001
2 0010
3 0010
Stepping back, let's now consider the original -2 And X < 2 parenthetical and look at the results from the True (-1) and False (0) possible outcomes for X < 2 after a bitwise And with -2:
-2 (1110) And True (1111) = 1110 = -2
-2 (1110) And False (0000) = 0000 = 0
Really the whole point here from using the -1 bit pattern is anything And True produces that same thing you started with, whereas anything And False produces all zeros.
So if X < 2 you get True, which results in -2; otherwise you end up with 0. It's interesting to note here that if our language used positive one for True, you'd end up with the same 0000 value doing a bitwise And with -2 that you get from False (1110 And 0001).
Now we know enough to look at some values for X and determine the result of the entire original expression. Any positive integer is greater than both -2 and 0, so the expression should result in True. Zero and -1 are similar: they are less than two, and so will be compared again only as greater than -2 and thus always result in True. Negative two, though, and anything below, should be False.
Unfortunately, this means you could simplify the entire expression down to X > -2. Either I'm wrong about operator precedence, my reference for negative integer bit patterns is wrong, you're using a version of VB that converts True to something other than -1, or this code is just way over-complicated from the get-go.
