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Acid strength is ranked by Ka, and the ratio of two Ka values says directly how much more readily one acid gives up its proton. Because pKa is logarithmic, each unit of pKa difference is a tenfold difference in Ka: acetic acid (1.8e-5) against chloroacetic acid (6.6e-4) is a 37-fold gap, about 1.56 pKa units.
Strength ratio
ratio = Ka2 / Ka1
Logarithmic gap
dpKa = pKa1 - pKa2
Yes - it is a tenfold difference in dissociation constant, which usually shows up clearly in reaction rate and equilibrium position.
Not directly. Convert the base to the Ka of its conjugate acid first, using Ka x Kb = Kw.