Possible on your first day. Look at the Trophy Cabinet and pick out one you feel you could do.
I did Pet Trainer awards. You can get 3 achievements going for this one.
I would chase my pet (walk/run in a circle) and when the music stopped I would wait a moment and the pet would get a desire bubble. Hold your hand over the bubble to start a Play game. When it's finished, start walking again.
To command your pet to sit, I had to put my hands on my thighs and pull them straight up. Chasing the tail was making a circle with your hand like you would with a real dog.
You could also try to get the tray for playing each Play game in free play 10 times.
Here is a list of all the Trophy Cabinet Awards.
http://www.xbox360achievements.org/forum/showthread.php?t=30...