There's good guidance in this thread...I would say, though, that there remain a lot of different ways to put together an OL winning team. In the past 6 months, I have won a few championships in OLs. Here are three of the teams, and yes there are some similarities, but there are a lot of differences too:
1.) Mega-platoon team (this was a lot of work to manage but a lot fun to see them succeed)
C: Platoon, Jack Lapp 1911, Shawn Wooten 2001
1B: Platoon, Jake Virtue 1890, Nap Lajoie 1896
2B: Platoon, 2009 Felipe Lopez, 1938 Jackie Hayes
3B: Platoon, 1954 Solly Hemus, 1922 Riggs Stephenson
SS: Platoon, 1993 Kevin Stocker, 1997 Barry Larkin
LF: 2018 Mallex Smith
CF: 1889 Walt Wilmot
RF: Platoon, 1944 Dick Wakefield plus AAA
SP: 1904 Joe McGinnity, 1904 Ja ck Powell, 1902 Bill Bernhard
2.) Cheap range with speed and 1890s hitters
C: 1922 Johnny Bassler
1B: Platoon, 2000 David Segui + AAA
2B: 1925 Frankie Frisch
3B: 1895 George Davis
SS: 1960 Maury Wills
LF: 1896 Tom McCreery
CF: 1889 Walt Wilmot
RF: 1942 Roy Cullenbine
SP: 1915 Dave Davenport, 1902 Bill Bernhard, 1919 Frank Miller
3.) HR power that normalizes well (aka the Buck Freeman team)
C: 1887 John Kerins
1B: 1901 Buck Freeman
2B: 1937 Billy Herman
3B: 2017 Marwin Gonzalez
SS: 1960 Maury Wills
LF: 1899 Buck Freeman
CF: 2019 Ketel Marte
RF: 2018 Mallex Smith
SP: 1920 Babe Adams, 1909 George McQuillan, 1915 Mike Prendergast, 1919 Frank Miller
And here's another team that just finished the regular season, won its division with 100+ wins:
C: Platoon, 1916 Wally Schang + AAA
1B: 1956 Wally Moon
2B: 1998 Roberto Alomar
3B: 1989 Bobby Bonilla
SS: 1923 Dave Bancroft
LF: 1889 Walt Wilmot
CF: 1984 Willie Wilson
RF: 1921 Max Carey
SP: 1904 Cy Young, 1915 Guy Morton, 1909 George McQuillan