Apple Mail Frustrations

Question

My wife and I are pulling our hair out trying to operate within Apple Mail. We are recent switchers and for some reason, the Mail program is causing the most trouble. Below are a few of our problems:
1. Her Address Book decides to delete all of the entries. She loses everything except for the Apple card and her personal card. We must revert to a backup.
2. When people view her emails and they have extra question marks throughout the entire message that were not typed. I've read about this in the forums but I haven't found a definitive fix for it. I can't even find an Apple acknowledgement for it.
3. This is a big one - sending emails using iPhoto 6.
If she is in iPhoto and wants to send a picture, she chooses the picture and clicks the "Send via email" (or whatever the button is). It creates a new message in Apple Mail. The picture displays within the body if the email and she is able to scale it down using the functions within Apple Mail. She is able to add text to the body of the email, etc. All is good.
She sends the email to me at work. I use MS Outlook XP on a Windows machine. When I receive the email, the picture comes as an attachment and not within the body of the email. Also, the comments she added to the email as well as her signature appear as attachements with a "ATTxxxxxxx.txt" type of file name. There are about 4 of them. One has the email text, another has the same text only with font information within it like:
<fontfamily><param>Lucida Grande</param>
</fontfamily><fontfamily><param>Helvetica</param>
</fontfamily>
It's ugly!
Now, as a test, within Apple Mail, she creates a new email. She clicks the add attachment button and navigates to where the picture resides and attaches it. Again, it appears within the body of the email and she can scale it. She can also add text to the body, etc. She sends that to me at work again. This time, the picture displays within the body of the email as expected, her signature displays correctly within the email, there are no extra attachments or any "ATTxxxxxxx.txt" attachments.
Why are we having so many problems using Apple Mail? These little things are causing us the most problems. They are very frustrating. We just want to use the email program and send photos, etc without thinking about it. It shouldn't be this difficult.
I'm just tired of my wife calling me at work crying because she can't get email to work right, and her Address Book decides it delete all of the entries from her address book and she has to start over (or revert to a backup).
Thank you for listening and helping.

Answer 1

Thanks for your reply.
Yes, I have been performing the daily/weekly/monthly maintenance.
The address book losing data is somewhat of a less concern for me. I always have backups. I'm just trying to get a good setup for my wife so she can send any kind of email she needs to and have it display reliably on whichever platform/client the receipient happens to be on. Yes, most of her contacts are Windows users who are probably using Outlook or Outlook Express, but there are a few Mac users as well.
I have run a number of tests using my Outlook at work and various web-based clients (Gmail and the web interface to my POP email) and Outlook is definitely the odd ball of the group -- surprise.
Some emails will display with pictures as attachments while others display with the picture embedded in the email. There is also an issue when you can type text at the top of an email, the embed a picture in the middle and type more text below the picture. When Outlook displays it, the text at the top displays in the body of the email, the picture shows as an attachment, and the text typed below the picture also displays as an attachment with an ATTxxxxxxx.txt file name. The contents only shows what you typed below the picture.
There's something with the attachment and the way Outlook displays it that's causing the problem. I even have it more narrowed down that this....
If the email is RTF with some sort of formatting in the message (colored text, etc) the entire message will display correctly in Outlook. The text at the top displays correctly, the picture shows as an embedded image, and the text below the picture correctly. However, if the email is Plain Text, it shows the extra attachments as described above with the ATTxxxxxxx.txt files.
I have also been switching between Text Encodings to try and figure this out. I saw a number of posts saying to use UTF-8 encoding. I have sent test emails using both Automatic as well as UTF-8 and I get the same results. I have also tried "Windows Friendly Attachments" and depending of the email, it still displays incorrectly.
There is also something strange with sending emails using iPhoto rather than attaching a photo through Finder. The email "Content-Type" is different between the two and both display differently in Outlook. If you attach through iPhoto, you get the extra TXT attachments, no matter the message format. If you attach via the Finder, if the message is RTF with formatting, it will display correctly. Strange!!
There's definintely an opportunity for improvements here. Problem is, I have no idea where to start. Hopefully someone has this figured out and may have some ideas.
Thanks!