Hello Serge,
It not clear what you are doing exactly, do you mean you parse text with BeautifulSoup before input it into the database field? And what is unacceptable?
About 1, I think previous question would help understand better the issue.
About 2, I don't see why it wouldn't work... But as I am not sure what you try to accomplish, I mean if you strip off tag with beatiful in the first place why add some tag back when you send the message...
I am sure we would benefit to see a bit of your code to bettter help you.
Note that HTML in email is a difficult topic as render engine are much less homogeneous in email client like outlook, thunderbird than what you may have from a normal browser. So having the right presentation everywhere is more difficult to achieve than a regular web page.
Good Luck
Richard