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First he was going to re-create pioneer Kiwi aviatrix Jean Batten's record-setting flight from England to New Zealand of 76 years ago, then he was going to base the plane at Te Anau where it would operate commercial scenic flights over Fiordland.
He managed the first part but the second is proving a challenge.
He needs $100,000 within the next month to enable the aircraft to pass its 100-hour check but says he does not have the money.
"I'm out of the frying pan into the fire. If I can't find a way to keep it here and make it pay for himself I will have to sell it," he said yesterday, hours after the plane landed at Te Anau Airport with himself and four others aboard.
There were potential buyers in the United States, he said.
In 1936, Batten became the first person to fly from England to New Zealand, a distance of 22,000km, arriving in Auckland 11 days and 45 minutes' flying time after her departure from the English county of Kent.
Mr Oremland owns Te Anau Lodge and said he wanted to cap off his adventure by landing in "the most beautiful part of New Zealand" and the town which is his home when he is in this country.
The sun shone, the mountains and lake glistened and about 250 appreciative spectators watched as the plane landed about 12.25pm. It was escorted on to the apron by two 1961 Rovers and a vintage fire engine.
Batten made her journey in a Percival Gull plane. Yesterday, a similar plane, a restored Percival Proctor from the Mandeville airfield near Gore, landed at Te Anau behind the DC3.
Te Anau had given the DC3 a "spectacular welcome", Mr Oremland said.
"There was no reception in Auckland for Jean Batten all those years ago, and now we had this welcome from a town which didn't even exist then. It was quite moving, actually."
The plane had been sitting on an English airfield for six years before Mr Oremland bought it on a whim. It was flown to France and underwent an extensive and expensive upgrade to gain its certificate of airworthiness.
The England to New Zealand trip had been satisfying but costlier than he expected, he said.
"I bought myself a trip of a lifetime, but I won't be doing that again."
Mr Oremland's next project is creating a language and linguistics permanent interactive exhibition in Paris.
"Life you only get once, and it is nice to touch as many different things as possible along the way."