
Since 2007 I've been driving this:

-its been a loyal thing, used mainly for school runs but more recently for my current job as an Uber driver. Its nearing 80k and never really was meant for ferrying customers around a college town, so I'm about ready to switch.
I have a decent idea of what I'm looking for (~2005+, <100k, <$14k, >25mpg, comfortable as a ride-share, and cheap to insure) but I haven't yet bought a car all on my own, so what I'm really after is just general advice. Time to buy for example, I've heard October is best to buy from dealerships but don't know if that applies for used cars.