Hey Jordwin!
I'm actually in the Kaplan class too and I've seen this exact question.
What we do know is that when we form a more stable alkene, more heat is released right? (ie. more exothermic, reaction more favorable), so a general rule we can see here is that the most stable alkene, when hydrogenated, will have the least/lower heat of hydrogenation since it has already released a whole bunch of heat getting formed.
What we're also doing is breaking the pi bond by hydrogenating, so think about it, if you're already stable, why would you want to hydrogenate the bond? THis would be extremely unfavorable thus the lower heat of hydrogenation.
So you would look for conjugation around the double bond or how substituted it is to rank the stability!
Hope this helps.