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Are you guys talking about the Henderson 4, The bike that was rebadged as an Indian? Or was it an Ace? Indian bought the rights to the 4 and did improve them, but was it really an Indian? I think the Triumph R3 has that market covered, sales of big bikes have slowed and I doubt there is room for 2 inline big inch bikes in the market place today. Fun to think about but probably won't happen.
You are correct that an inline 4 very likely would not sell. They can push all the power they need with a twin.
Indian bought Ace. Ace was designed my Mr. Henderson but was not a Henderson 4 because Schwinn owned all those patents. I think Indian altered the ACE a lot in the 30s. I am talking the Indian inline 4. The 41 was the last year and is sought after by collectors. It was also the most powerful.
Dog! In average condition I assume your friend knows he is using a very valuable bike as a daily rider. They even have one in the freaking Smithsonian! If he falls off, they should put the bike in the ambulance! 
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1941 Indian
FOUR CYLINDER MODEL 441 78ci
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