Originally Posted by HavocSteve
You would have to go in and sit down with a salesman. They should be able to bring it down but some don't budget at all. What the price is listed at is where they stay. Start looking at actual T+C BMW or Endras or even Toronto BMW. Look at some CPO 323i's that will come with a factory warranty and also the extra extended warranty on top. That way you get comfort of mind and hassle free issues.
A CPO 323i or 328i would be perfect for you. Also, remember that you needn't spend your entire budget! A 2009 328i with reasonable mileage would fit nicely within your stated budget and leave you with cash for winter tires or some other small modifications.
Also: I wouldn't price in a ten-plus percent discount. You should budget according to list prices.
To answer your direct questions:
1. The 2010 335i was a fine car. The fifth generation 3-Series (E90) sedan was current from 2006 to 2012 and saw a small mid-cycle freshening in 2009, so you shouldn't encounter any substantive differences between similarly equipped 2009 and 2010 examples.
2. 3-Series residual values are relatively linear. The Honda example you cited (2012 Civic -- not a bad car, just underwhelming relative to its predecessors) doesn't have an immediate analogue among mainstream BMWs.