Well...why isn't SOMEONE in the business of running special trains like this, if there is profit to be made? Any money-losing entity such as Metro-North should be finding ways to make a profit on even small things, to offset subsidies from taxpayers.
Well...You could contact Amtrak or Metro North to run a charter train using their equipment. If you were to run as this one did, GCT to Poughkeepsie, you would probably be the only one on it, as most would say "I'll just take a regular Metro North train. It's cheaper."
So, now you need to take a fleet of older cars, refurbish them and bring them up to current standards that railroads will accept them. Many private car owners that do this spend hundreds of thousands of dollars to do just that. Once that is done, you'll need to pay a huge sum just to ferry the equipment where you'd like it to run, and then pay for the railroad to charter a crew and locomotives. Let's not forget about liability insurance. The ticket prices for such an excursion would be fairly large to offset the costs (I've heard the cost to ride that train was about $1,000 a pop). So as far as you chartering a train to make a profit, there isn't all that much to be made on something like this.
As for Metro North finding ways to turn a profit, government agencies do not operate like that. If they make a profit or break even, they lose their subsidies. So there is no incentive for them to attempt to make a profit.
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