You can't effectively foam roll / massage the IT band. It is simply too strong. A pair of hands / your bodyweight are not strong enough to meaningfully loosen up the tissue. You need to figure out why it's tight (if it's tight at all) and correct that issue. The most common thing when it comes to the knee is the feet turn out too much in relation to the knee. This is often from tight peroneals: Read #2 here: http://b-reddy.org/2011/08/04/3-common-tight-muscles/
The peroneals and IT band are connected. Could be why you are so tender at the IT band. Tough to say without seeing you move.
Prolotherapy is worthless crap. Save your money.