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If you are inviting 200 guests to your wedding, do you have to handwrite out the addressing on every single wedding invitation that you are planning to send out? If you are, don't do them all in one go, because the ones at the end of the stack will definitely have worse handwriting than those at the beginning. Traditionalists will insist on addressing wedding invitations by hand because it personalizes the invitation even if they are custom printed.
What does it say about you if you choose to forgo handwriting the addresses on each and every envelope? Nothing. Don't worry about it at all. Most people don't even look at the envelope. They are far more interested in the invitation inside the envelope.
If you really want to do the addressing by hand, then be sure to set aside enough time to address only a few wedding invitations at a time to ensure the quality of the writing. If you or someone in your family is good with calligraphy, this might be a time to enlist their assistance in addressing wedding invitations.