In general, this is difficult and doing some work outside of the RE (as suggested in the comment by M. Buettner) is often required. Your problem is easier because it can be reduced to a pattern with only one repeating element.
You have one or more letters, followed by one or more of (letter, digit, dot, hyphen) followed by a single (letter or digit), right? If so, the repetition of the first group is not needed. Leave off the + to get
r"^[a-zA-Z][a-zA-Z0-9\.\-]+[a-zA-Z0-9]$"
and you will match exactly the same set of strings. Any extra leading letters past the first will be matched in the second group instead of the first.
Now, the only variable portion of your RE is the middle section. To limit the overall length to 30, all you need do is limit that middle portion to 28 characters. Change the + to {1,28} to get:
r"^[a-zA-Z][a-zA-Z0-9\.\-]{1,28}[a-zA-Z0-9]$"
You can read more about Python REs at:
http://docs.python.org/2/library/re.html
a-be valid? Would-be valid? What about0? You need to think your question through more.