Why is the boiling point of alkyl iodide is more than alkyl fluoride?
The main factor affecting the boiling point is the molecular weight, as can be pictured from the noble gases boiling point in the periodic table (the noble gases are those which have the weakest interactions due to their complete outer shell). But note that if you want to consider all the effects altogether, you must use Kelvins instead of Celsius. So going from 44°C to 88°C is not twice as much but a mere 14% increase.

The other factor affecting boiling point is the nature and strength of intermolecular interactions, usually in the order ionic > hydrogen bond > dipole-dipole > Van der Waals.

In the comparison of RF vs RI boiling point, molecular weight is definitely in favor of higher boiling points for RI, at least for small molecules. It is true that the C-F bond is much more ionized than C-I so it will create stronger dipole-dipole interactions but not sufficiently to compensate for the effect of the mass increase.

HTH