With practice, you'll pick this achievement up no problem.
Select 'easy street' and lets begin!
The first bundle you'll see is on the pavement when you come to door number 118 (the third house).
The second bundle is on the left side of the road at door number 115 (the sixth house).
The third bundle is on the pavement inbetween door numbers 112 and 111 (the ninth and tenth house.)
The fourth bundle is on the pavement at door number 109 (the twelveth house).
And the fifth bundle is in the left side of the road at door number 106 (the fifteenth house)
This is the shortest way to get the achievement but by all means you can pick up any bundle of papers you want as long as you total five bundles in one life.
Also, your not timed on this achievement so take your time to avoid drains, breakdancers and the like. I will point out that you have no need to be on the right side of the road as there is only cars waiting to run you down.
Halfway through the route (after door number 111), SLOW DOWN! Take your time passing the traffic coming from the left side otherwise you'll end up with that lovable paper bag over your head.
And that's achievement unlocked!