Seems like I could spend 10-11 k on a Cruze of that year with the options I want.
Civic seems to be more 15-16k.
The other thing I'm worried about is insurance prices, being 21 years old it isn't cheap.
From what people have told me the civic is more to insure.
Right now I pay 250\month for a 2001 ford escape
It's no secret Civics are more to insure, even older ones. Also no secret, that they range 15-25% more than an equivalent domestic, or Korean make. Mid size sedans, like the mentioned Fusion, are cheaper to insure. I would "focus" on them. Usually has more equipment, more power, safer, and only consumes slightly more fuel (if you stick with a 4 cylinder).
As for as infotainment, I would be too concerned with that. If the car your looking meets your needs great, if not, spend $500 and get an aftermarket deck. That's what I did with my Honda Odyssey. Bought a deck online, removed the old one from a YouTube video, had the local radio store wire it for $30, and that's it.
I would look at 1st gen Fusions (around 09-12), 2nd gen Mazda6 (same years), Malibu (boring, but some great deals), can't comment much on Chryslers. Maybe the Sonata, and Optima.
This looks pretty good:
http://www.autotrader.ca/a/Mazda/MAZDA6/Mississauga/Ontario/5_24891863_ON20080721120343642/?ursrc=ppl&showcpo=ShowCPO