Yes i tend to think short steep hills are harder than the longer more shallow hills - on very steep hills i find the pedals just wont go round , particularly having lost a bit of bodyweight.
Its a while since i was on stanmore hill , i always use clamp hill as my doorway into stanmore - i will have to try it. All those roads north off the A404 are hills - when i first started cycling i was cycling home from northwood up the watford road A4125 and just gave up, collapsed. A lycra clad superhero cycling past called out to inquire if i was ok , to which i made the universally recognised sign for having a heart attack but he surprisingly didnt stop. Things do get slightly easier.
Mind you - youve got an expensive new bike so all those hills should be easy for you.