Let $\ce{R-OH}$ be a group with a $pK_a$ of 16. Are the following two statements correct?
In principle, the group can protonate another acid with $pK_a > 16$, and so (put differently), any "acid" with $pK_a > 16$ can be used to "deprotonate" the group
If I had a table with bases were only $pK_b$ values were given, in order to select these bases from the table which are able to deprotonate the group, I would need to choose the bases with $pK_b < -2$ because the $pK_a$ values of their conjugate acids (i.e. $pK_{a\text{H}}$) will be 16 or higher.