Is there a good reason I see VARCHAR(255) used so often (as opposed to another length)?
255 is used because it's the largest number of characters that can be counted with an 8-bit number. It maximizes the use of the 8-bit count, without frivolously requiring another whole byte to count the characters above 255.
When used this way, VarChar only uses the number of bytes + 1 to store your text, so you might as well set it to 255, unless you want a hard limit (like 50) on the number of characters in the field.
Historically, 255 characters has often been the maximum length of a VARCHAR in some DBMSes, and it sometimes still winds up being the effective maximum if you want to use UTF-8 and have the column indexed (because of index length limitations).
Probably because both SQL Server and Sybase (to name two I am familiar with) used to have a 255 character maximum in the number of characters in a VARCHAR column. For SQL Server, this changed in version 7 in 1996/1997 or so... but old habits sometimes die hard.