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You get a bonus when you deliver them all. Make sure to grab the newspaper on the tip and let it hang. Then shove the top into the mailbox first. Its very very hard if you grab the paper in the middle.
Kevin
I'll get to it now I'm back in the game.
alternatively: babysit then focus on pizza delivery.
basically all I am saying is pizza delivery is worth your time and doesn't run into a "pizza still in delivery box bug". I do two or three 5-pizza deliveries a day on my current survival save, when I need cash.
FYI pizza costs $7. you get $15 upon delivery, and anywhere from $6.50 to $2.00 depending on time remaining when delivered. you won't get many max tips doing five deliveries at once but just doubling investment is worth the short time it takes to do IMO