Your objective is unclear to me. I would imagine that the deflection at the applied point would be exaggerated, but totally depends on your goal with this simulation.
First off, conformal mesh will not allow the parts to move relative to each other, you want separate parts. I would try using two contacts, one "no separation" for the sliding in the hole; and frictionless or frictional for the other one. The contact faces selected are very large and will...
Review the solver output text in "solution information" > "solver output". There ought to be warning and/or error messages describing why the calculation is failing to converge. It will typically be due to inadequate boundary conditions, errors in contact setup or overlapping or disconnected...
You ought to be able to export the resultant geometry and save as a file (this step can be time consuming), then import said file into whatever geometry editor you're using in the future simulation. The geometry typically requires a bit of cleanup and smoothing beforehand, though.
