Police launched Operation Kite in 2014 to investigate a string of fraud allegations with Bennett a person of interest in a fraud investigation.
It related to selling watches on Trade Me and brokering helicopter deals dating back to 1998.
Bennett is accused of a total of 60 varying offences between June 2007 and February 6, 2015, across New Zealand, including Auckland, Manukau, Whangarei, Paihia, Taupo, Palmerston North, Upper Hutt, Christchurch, Cust, Wanaka, Naseby, and Invercargill.
They include allegations that along with now estranged wife Simone Wright, he indecently assaulted a 15-year-old girl on two occasions between March 28 and April 1, 2008.
Bennett is also accused of supplying the teenager the class B drug MDMA, or ecstasy.
Many of the charges allege that he used documents dishonestly and without claim of right to obtains hundreds of thousands of dollars. He's also accused of selling a fake Rolex watch.
Between January 26 and February 6 last year he is accused of stealing, alongside Wright, a Beau Birdsall 45 cutter yacht worth $145,000 from Paihia.
The Civil Aviation Authority (CAA) has also filed 12 new charges, which alleged Bennett flew a Eurocopter AS350B2 helicopter on six occasions across New Zealand, including Hamilton, Upper Hutt, Paraparaumu, and Christchurch, between March 22 and April 21, 2014 without holding a private pilot's licence and without an appropriate current medical certificate.
Bennett and Wright were arrested in February last year as they sailed into Sydney Harbour from Northland on board a crippled yacht.