So far, I'm thinking of this as an "interesting possible connection" between Reuben Wells and Reuben's Train - but I'm not ready to accept it as fact. Maybe this will be a question that will remain open at Mudcat for years, until we find something that ties it all together.
Good sleuthing - but to me, still inconclusive.
-Joe-

For the sake of discussion, here are the two versions we have in the Digital Tradition:

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REUBEN'S TRAIN

Ol Reuben made a train & he put it on a track
He ran it to the Lord knows where
Oh me, oh my ran it to the Lord knows where

Should been in town when Reuben's train went down
You could hear that whistle blow 100 miles
Oh me, oh my you could hear the whistle blow 100 miles

Last night I lay in jail had no money to go my bail
Lord how it sleeted & it snowed
Oh me, oh my Lord how it sleeted & it snowed

I've been to the East, I've been to the West
I'm going where the chilly winds don't blow
Oh me, oh my I'm going where the chilly winds don't blow

Oh the train that I ride is 100 coaches long
You can hear the whistle blow 100 miles
Oh me, oh my you can hear the whistle blow 100 miles

I got myself a blade, laid Reuben in the shade,
I'm startin' me a graveyard of my own.
Oh, me, oh lordy my, startin' me a graveyard of my own.

Repeat 1st verse

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REUBEN TRAIN
(traditional)

Oh, Reuben's coming down the track,
And he's got his throttle back,
And the rails are a-carrying him from home.

If the boiler don't bust
'Cause it's eat up with rust,
I'll soon be a long ways from home.

If you don't believe I'm gone,
Look at the train I'm on;
You can hear the whistle blow a thousand miles.

I'm a-going down the track;
I ain't never coming back,
And I'll never get no letter from my home.

Well, the train run so fast
Till I knowed it couldn't last,
For the wheels was a-burning up the rail.

Old Reuben had a wreck
And it broke old Reuben's neck,
And it never hurt a hair on my head.

Now I'm walking up the track,
Hoping I'll get back;
I'm a thousand miles away from home.

If I ever get back to you,
You can beat me black and blue,
For I'll never leave my shanty home.

Collected by Sandy Paton from Frank Proffitt, Reese, North Carolina, 1961.
Lomax printed a collated version of eight stanzas "picked up through the years
along the song-hunting trail" (The Folksongs of North America, New York, 1960).
The Frank C. Brown Collection (North Carolina Folklore, Durham, NC, 1952)
includes two versions, one of which contains seven stanzas. The song, in more
fragmentary form, seems to be quite widely known. Its relationship to the
well-known "900 Miles" is obvious, I think.

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And the Traditional Ballad Index entry on this song:

Reuben's Train

DESCRIPTION: Lyric piece about Reuben's train and travels. Versions vary widely; most contain a verse something like this: "Reuben had a train and he put it on the track, Hear the whistle blow a hundred miles."
AUTHOR: unknown
EARLIEST DATE: 1927 (recording, Grayson & Whitter, as "Train 45")
KEYWORDS: train nonballad
FOUND IN: US(SE)
REFERENCES (5 citations):
Cohen-LSRail, pp. 503-517, "Reuben's Train/Train 45/900 Miles" (2 texts plus exceprts equivalent to about three more, 2 tunes; the first text is close to "Reuben's Train," the second to "Nine Hundred Miles," but the article is mostly devoted to showing how the two songs mix)
BrownIII 236, "Reuben's Train" (2 texts, with "A" being closer to "Nine Hundred Miles" than "B")
BrownSchinhanV 236, "Reuben's Train" (3 tunes plus text excerpts)
Warner 133, "Reuben's Train" (1 text, 1 tune)
Lomax-FSNA 302, "Reuben" (1 text, 1 tune)
Roud #3423
RECORDINGS:
Emry Arthur, "Reuben Oh Reuben" (Paramount 3295, c. 1931; on BefBlues2)
Dock Boggs, "Ruben's Train" (on Boggs3, BoggsCD1)
Carolina Ramblers String Band, "Ruben's Train" (Banner 33085/Romeo 5345, 1934; Melotone M-13947, c. 1935)
Bill Cornett ,"Old Reuben" (on MMOKCD)
Elizabeth Cotten, "Ruben" (on Cotten02)
[G. B.] Grayson & [Henry] Whitter, "Train 45" (Victor 21189, 1928, rec. 1927, on GraysonWhitter01) (Gennett 6320, 1927/Champion 15447 [as by Norman Gayle], 1928)
Vester Jones, "Old Reuben" (on GraysonCarroll1)
J. E. Mainer's Mountaineers [or Wade Mainer], "Riding on Train Forty-Five" (Bluebird B-7298, 1937; Victor 27493, 1941)
Wade Mainer & the Sons of the Mountaineers, "Old Reuben" (Bluebird B-8990, 1941)
New Lost City Ramblers, "Riding on That Train 45" (on NLCR06, NLCRCD2; on ClassRR [as "Train 45"])
Poplin Family, "Reuben" (on Poplin01)
Wade Ward, "Old Reuben" [instrumental] (on Holcomb-Ward1)
Doc Watson, "Old Ruben" (on Ashley02, WatsonAshley01)
CROSS-REFERENCES:
cf. "Nine Hundred Miles"
cf. "Rain and Snow"
SAME TUNE:
Jack O'Diamond Blues (recorded by Blind Lemon Jefferson)
ALTERNATE TITLES:
Old Reuben
NOTES: I know two tunes for this piece. One resembles "Nine Hundred Miles" and "Rain and Snow"; these three songs seems to have cross-fertilized (so much so, in fact, that I literally cannot tell which one was the more direct ancestor of the Grayson & Whitter recording; I placed it there almost arbitrarily).
The other is that used by Frank Proffitt, who said of it, "This is one of the oldest simple banjo tunes.... It was generally the first tune learned, by playing two strings. There are about fifty different verses to this" (quoted by Warner).
G. B. Grayson is said to have turned "Reuben's Train" into "Train 45" -- but they are still so close that I think they can be considered one song. - RBW
Last updated in version 4.1
File: Wa133

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