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I don't think Colt will refinish a gun that old.
There's always the problem of opening the gun and finding a safety issue, and not having parts to correct it so Colt usually won't do any work on older guns.

Good sources of a refinish are Ford's, Glenrock, and if you want a finish more "correct" for that era there's Turnbull's.
Turnbull's is a restoration service and are EXPENSIVE.
Ford's and Glenrock do top quality work using modern hot salts bluing.

Ford's Custom Gun Refinishing - Ford's Desert Eagle Sights

Glenrock Blue

Turnbull Mfg. Co. for firearm restoration of antique guns - antique revolvers, antique pistols - including 1886 Winchester rifles, Marlin rifles, Parker shotguns, Colt revolvers, and more

As for whether to have it refinished, much depends on the condition of the gun and finish. Refinishing a 1909 Colt Police Positive is not going to increase the value, and again, depending on how much original finish is left, may decrease the value.
 

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Best option is to have Colt refinish the cylinder.
The plating should not have flaked off, but at this late date I doubt that Colt will do it for free.

They can refinish it and it's unlikely even an expert could tell it was re-done. There should be no issues with matching the original finish.

I suspect the best way to deal with it is to send the entire cylinder and crane assembly in, rather than risk damaging it by attempting disassembly.
Back then the cylinders were much more difficult and risky to disassemble and you need a special wrench to do it.
Just contact Colt to get the details straight, then you can mail the cylinder through the US Post Office well insured, or sent it through UPS or Fed-Ex without having to pay a significant amount of money for shipping the entire gun.

To remove the cylinder assembly, just unscrew the cap screw on the right front side of the frame and remove the spring and plunger under the cap.
Rotate the cylinder so a flute lines up with the lower front of the frame and gently slide the entire assemble forward.

Make sure to use a real gunsmiths screwdriver bit to remove the screw to avoid damaging the slot.
The right driver bit can be bought from Brownell's.
It would be a Magna-Tip bit # .210-3:

Magna-Tip Bits | Screwdrivers & Sets at Brownells
 
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