How do ionic, polar, hydrogen-bonding and non-polar compounds compare in TLC? $R_\mathrm{f}$ decreases with increasing polarity. Does this mean a compound with an ionic bond would have the lowest $R_\mathrm{f}$? And nonpolar would have the highest $R_\mathrm{f}$?

Example: $\ce{RCOO- Na+}$ is ionic.  If the above is true it should have a lower $R_\mathrm{f}$ than cyclohexanol which has H-bonding?
No, your analysis is wrong. 

The nice thing about TLC is that you can pick the "paper" and the solvent to suit your analysis. So if you use benzene as the solvent then it won't "drag" ionized compounds along behind the solvent front very well.  If you use water ionized compounds do get dragged along nicely.