(I hope this is right...)
Played twice. The first game was without the Office expansion. While I considered using it just to get the extra 4 turns, I decided to just play as is.
Didn't remember to discard from the supply until I had played a couple of turns. The discard really didn't seem to play into any kind of strategy- I discarded the higher cost cards at first since I just couldn't earn enough coins early on.
I did finally start getting enough coins and started tossing the Convenience Store and Hospital cards. Neither of those really seemed to be able to help quick enough, since the supply is quite limited.
I didn't win. I got as many as 7 win icons before I ran into too many sad faces. I flipped as many of the Residential Area cards as I could so I could avoid playing them. I guess I just didn't do that fast enough.
On to game 2. I added in the Office expansion. It didn't say to add any of those to my hand, so I just put the four cards into the supply. At first look, it the Office card doesn't seem to do much- it's the first card you play and gives you a coin. I thought the four extra turns would help. Nope.
Going on what I did in the first game, I tried to flip as many Residential cards as I could. I did get one Office card, then made the other expendable. Still didn't get many (any?) Hospital cards and worked on getting the Central Park cards. I also chose to shuffle my discards back into my hand if my hand was low. I would have enough cards to play and get some coins, but it would also cost me another turn. So I would just set the office card down first, shuffle, then play.
I got as many as 7 award icons before I'd run out of cards to play, or would hit my sad face limit. And yes, I lost.
This will take a bit more thinking (and reading on BGG) to get it. It would probably help if I wasn't trying to watch the Sugar Bowl at the same time...
In the beginning I didn't flip the Residencial Areas, I decided to risk more and push my luck. When I had two frownies I stopped and purchased the convenient store. Sometimes I got further and bought the hospital, allowing me to risk even more. I managed to beat the game with just one card in the supply left. I made sure to play only the cards I really needed and prevent my deck from running out too early, because reshuffling it would mean to discard one card from the supply.