I used to deliver games all the time to people. Only ran into a problem twice. Once was when I did not get the money before hand and got the game all set up in the guys basement. When I got ready to leave and asked for payment, there was a short sparkle in the fellows eye that indicated he was thinking about not paying. The other time was just a total mess and I won't go into details.
Rule of thumb, unless you are insured or super desperate to unload the game, avoid anything but curbside delivery. The "nice guys finish last" saying applies here.
Now if it's a good friend you have known for years, of course help him out.