It does appear, circumstantially, that Winfield checked into a Chicago Hotel in 1891. A "stub" from the Chicago Tribune for 14 February 1891 (pay per view) shows him listed. It is attached, apparently, to the bottom of an embezzlement scandal, but Chrispy thinks this is a coincidence, as hotel registries were often appended to other news columns.
Once more newspapers are scanned into the digital archives, we should be able to make more tracings of his circuit riding. Obviously Chicago and 1891 are pretty critical, as he was now married with a child, and in two years hence he will have collapsed with illness.
If anyone has access to the more Jeweler's Circular and Horological Reviews of the era, Frederick A Lovecraft is mentioned in connection to his suicide, and it's possible that George Lovecraft might be mentioned. I've not traced WSL in it.
Here are the ones I've examined (google books)
Vol 15, 1884
Vol 23, 1891
Vol 27, 1893
Vol 34, 1897
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