Of course, Democrats would face a split between gold and silver forces even had the GOP won in 1892; but whichever faction won the Democratic nomination in 1896 would probably win the election and would get credit for the recovery of the late 1890s.)
Big question: who would the Democrats nominate in 1892? Would the Populists still rise separately, or join with other silverites to wrest the Democrat nomination from the Bourbon faction? ISTM that an outright silverite campaign by the Democrats could lose very badly.
Another point, perhaps not real but to be considered: the Republican 51st Congress of 1889-1891 created six new states in the Northwest: Washington, Idaho, Montana, Wyoming. South Dakota, and North Dakota. I doubt if the Democrats would do that; the new states elected 12 new Senators and 7 new Representatives, all Republicans.
Before the admissions, the House was Republican by just four seats OTL; the Senate by just 1, making these bills hard to pass, I think. The 1% shift in votes required to flip NY would almost certainly flip a few House seats. In any case, statehood bills must be signed by the President or passed over his veto. Cleveland would not sign the statehood bills and Congress would not override the vetoes.
Except I'm wrong. Statehood for South Dakota, North Dakota, Montana, and Washington was passed in the last days of the 50th Congress (22 February 1889), when the House had a Democrat majority (167-161) and Cleveland was President. Those four states were
formally admitted later in the year, but statehood was already a done deal, and apparently with Democrat support. (Idaho and Wyoming were granted statehood and formally admitted later in 1889-1890.) So the process would not have been affected by Cleveland's re-election in 1888.
Oh well.