To expand on abell's excellent point in simpler words:

you'll have a greater chance of finding the word starting with a letter that more commonly starts words than other letters.

That won't reduce the length of your search, because the fact that it is more probable that a word starts with a certain letter means there are more words starting with that letter. So you are more likely to find the password in that subset, but to exhaust that subset you will have to make more guesses, so that you can make no fewer guesses regardless which way you choose to order them.

In effect, any approach of changing the order of guesses can be mapped to linear scanning of entries in an accordingly shuffled list of words. Once you realize that it is easy to see that there is absolutely no way to guess the right word in less than (dictionary size / 2) attempts on average.

Makeshifts last the longest.

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