If you are spending money on gorgeous stationery and beautiful hand calligraphy take the time to get your envelopes hand-canceled!
Okay, so I may be jumping the gun, a lot of people don't know what hand-canceling an envelope is. Typically when you put a card in the mailbox to be delivered, the mail will then be brought to a canceling machine (this is most likely not the technical term) This machine has rollers that push all the mail through and cancel each stamp showing it has been processed.
These machines aren't necessarily meant to read beautiful modern calligraphy.... they also are not meant to push through envelopes that have bows or thick paper inside. Ooo silk ribbon and 220lb stock <3333. Envelopes that are pushed through these rollers go through some serious wear and tear.
You can actually request for your envelopes to be hand-cancelled this is where the post lady or gentleman will cancel the stamp by hand. This way your envelope will not need to be put into the canceling machine and will in most cases (I found nothing is 100% guaranteed when it comes to the Post office) be delivered in much more pristine condition than a machine cancelled envelope.
So if you are spending the money on pretty stationery always pay to hand-cancel them, it's totally worth it!
A few tips for a hand-canceled envelope.
If you split up your envelopes into smaller, more manageable batches a lot of time the post people won't charge to hand-cancel them.
Try to head to the post office when it isn't a busy time (like a week before the holidays). I bet you will find the mail people very appreciative that they don't have to hand-cancel 150 envelopes with a line of people out the door waiting to be helped!
Call ahead to a few different Post Offices and ask what they would charge to hand-cancel
Be friendly - it can go a long way!