Just One of Those Mondays!

I have been trying to send out my prayer letter update since before Christmas, but without success! Here's what I've done so far:
Laid it all out in Microsoft Publisher, then saved it as a PDF file, as well as a jpeg file.
Attached the PDF to my email, then added all the addresses of the recipients (in the BCC field)
Hit the send button.
But wait! Error! The email told me that it couldn't send due to a connection error!
I attempted again, only this time with a jpeg file. Same results.
Again, only I typed in all of the addresses. Same results
Yet again, but I split up the amount of addresses. The same results.
I tried many different ways, even using two different email addresses, but it was all the same. It wouldn't send!
Finally, I sent each email individually, taking 2 hours. Success! The prayer letter finally went through!
But wait! It's not over yet. I began getting emails back from people saying that they couldn't read the font. It was too small. So I have tried, yet again, to deliver my letter bulk instead of individually. This time I just copied the text into the email, but it STILL WON'T SEND!
What should I do? Please, if anyone has any possible idea what could be wrong, I'd like to know! Otherwise, every time I send out a letter I'll have to be prepared to send it individually to over 100 people! I know it's still faster than sending it snail-mail (and a money saver), but I'd really like to find out if it's operator's error or something wrong with my email(s).
HELP!