Determining which acid is stronger

[Ashley Johnson 2G]

I am confused if the bond length or electronegativity is more important to determine acidity?
For comparing two compounds, such as HCl or HI, HI would be stronger because it has a weaker/longer bond.
For comparing HBrO2 and HClO2, I thought that bond length would also determine strength here, as the Br/Cl atoms are directly attached to the hydrogen, but it is actually determined by electronegativity. Since there is an O, is that why electronegitivity determines it in this case?

Thanks

[Mark_Botros_1D]

For HBrO2 and HClO2, the Br and Cl atoms are not directly bound to the hydrogen. Therefore, since Cl is more electronegative than Br, it has a greater electron-pulling power to weaken the OH bond. Therefore, HClO2 is a stronger atom.

[Joan Moci 1J]

In HCl and HI, the hydrogen is bonded directly to the Cl or I. This means that the longer the bond, the weaker it is and the easier it is for the hydrogen to be removed, making HI the stronger acid as the bond between the I and the hydrogen is longer/weaker than the bond in HCl between the Cl and the H. However in HClO2 and HBrO2, the hydrogen is bonded to one of the oxygens. As a result, since Cl is more electronegative than Br, it pulls the negative charge from the O more when it becomes O-, which delocalizes the negative charge and makes the resulting anion more stable, making HClO2 the stronger acid. Essentially you need to look at what the hydrogen is bonded to.

[Anthony_Rio_3K]

What are general strategies for determining strong and weak acids and bases? Anything other than memorization?