The '53 Windsor six is, if i mistake not, a 265cid flathead--something that several Inliners would like to have for a project. A 1960s MOPAR inline six would be, at best, a 225cid overhead--a great little engine, but a mismatch in this application, especially with an automatic transmission. The 265cid long-stroke flathead provides much more low- and mid-range torque to motorvate a large and *heavy* vehicle, which the Windsor surely is.
If one wants to abandon the fluid drive, then the best alternative is probably a standard transmission (and overdrive, if possible) from a Desoto or Dodge of the period. If one must have an automatic, then one must be prepared to spend time, money and hard labor. Machine tools will be necessary.
God's Peace to you.
d
Inliner #1450