In the book, Wade Organic Chemistry, 8th edition, exercise 4-57, the correct answer is given as:

cp - cyclopentyl

initiation:
HOOH -> 2HO* deltaH=+213 kJ/mol
HO* + I-CI3 -> IOH + CI3 deltaH = -46 kJ/mol

propagation:
cp-H + *CI3 -> cp* + H-CI3 deltaH = -21 kJ/mol
cp* + I-CI3 -> cp-I + *CI3 deltaH = -34 kJ/mol

The overall deltaH is -55kJ/mol for the propagation steps. I have a significantly more exothermic process here:

initiation:
HOOH -> 2HO*
cp-H + OH* -> cp* + H2O deltaH = -101 kJ/mol

propagation:
cp* + I3C-I -> cp-I + I3C* deltaH = -135 kJ/mol
I3C* + cp-H -> cp* + I3C-H deltaH = -21 kJ/mol

Here the initiation is less endothermic, and the propagation is significantly more exothermic. So why is this not given as the correct answer? Am I missing something here? I'm quite a newb at organic chemistry, so I think I must be wrong, not the textbook.

The energetics are calculated using bond dissociation enthalpies, found in the book itself.