Here is a some string help site:
http://www.fretnotguitarrepair.com/stringing.htm

Here is another:
http://www.wholenote.com/default.asp?iTarget=http%3A//www.wholenote.com/cgi-bin/page_view.pl%3Fl%3D577

As for # of times the string wraps the peg...2-3 is about right.

As far as different tunings wrecking your neck..I don't know. Most people drop tune so this will decrease the pressure on the neck. For the Allmans Rambling Man you need to tune up I can't remember if its a half or full step but even that the neck should still be fine. I'm assuming you have an electric guitar. Putting heavy gauge steel strings on a classical guitar will kill it.

Just my 2cents...Hope it helps