To buy, or not to buy, a car--that is the question (containing within it multitudes)

First of all, any car manufactured in the last year or three that has a stereo more complicated than a radio is going to have a line-in somewhere. So you can hook up any mp3 player you want for the cost of a $3 cable. Second, hybrids aren't the only way to do fuel efficiency. Hell, the http://www.cars.com/honda/civic/2010/ does 29-36mpg out of the box. The http://www.cars.com/honda/fit/2010/ does 33-35mpg. Hybrids are cool and all, but if what you're really worried about is efficiency as such rather than coolness, there are other options which are more efficient than your current vehicle and can be substantially cheaper than a hybrid, even allowing for differences in fuel efficiency. It'll cost you $1225 to drive a vehicle which gets 43mpg 15,000, but it'll only cost you $1750 to drive a vehicle getting 30mpg the same distance. That's $500, which ain't nothing. But a hybrid could cost you can extra $5,000 in purchase price, meaning it could easily take you ten years to make up the difference in cost by savings on fuel. Take the money, say thank you, and get yourself a Civic or something.

The 2009-2010 Honda Fit Sports have USB stereo input, as well as aux line in. They also get respectable gas mileage and have excellent, usable, interior space. Any late model stereo with an aux input will allow you to use your ipod as an input source, though you'll need to select the song on the ipod directly. This turns out to be superior to most stereo integrations.

I bought a 2010 Honda Insight last year (after my 2005 Honda Civic Hybrid was totaled by an asshole bad driver who t-boned me). I LOVE the Insight. It's small, but comfortable, with massive cargo space. It drives really well, is zippy, and has the tiniest turning radius of any car I've ever been in. We regularly got ~45 mph in the Civic Hybrid--please note that starting in 2006 the Civics are a lot bigger than my 2005 was and the hybrid doesn't get nearly as good mileage now--and the Insight is pretty similar. We considered the Prius, but I just don't enjoy its annoying bells and whistles, like the massive touchscreen and the non-key key-thing. I test drove a Fit, and liked it a lot (the Insight is built on the fit body). But ultimately the Insight had everything I wanted and is a delight to drive. The bottom end 2011 model retails for ~$18,000. If you're considering the Fit and Prius, definitely check out the Insight.

All car characteristics aside: this is a gift from your folks to significantly reduce your expenses and your risk, in terms of safety and piece of mind. Let them buy you a car, take a vehicle maintenance course while you're still looking for that teaching position, and keep the car so well-maintained that you won't need to worry about your transportation for the next five or six years.

What I would do is: 1. Go to Edmunds or Consumer Reports and see what their "top picks" are for different categories of car (eg small, hybrid, commuter, etc). This gives you a starting point. Write down those model names. 2. Go to a used car website and look up the range of model years of cars you're interested in, in your area. Figure out what model years are within your budget for these cars. (For example, it looks like 2008 Priuses are in the 18K-23K range for San Francisco. 2009 Civic Hybrids are in a similar price range.) These will be the model years you'll research. 3. Go back to Edmunds and/or Consumer Reports (CR requires a subscription but has more complete information) and find out everything you can about the model years you're considering. Some years are bad, some years are good. Sometimes they do a redesign so the difference between say the 2005 and the 2006 is much bigger than the difference between the 2006 and 2007 models. Sometimes they change parts-suppliers, and you can get a whole year worth of cars that have bad transmissions. Sometimes they upgrade major safety features, eg adding airbags or electronic stability control. You want to find out if any of the model years you're considering are much better or worse, or if you can shave off some money by buying a year-older car that is basically the same car with just a few more miles. 4. Go back to the used car sites and make a list of where your target model-years are being offered (in certified models, in the color you like, whatever), and at what prices. 5. Now you're thinking about price and your buying strategy. http://www.edmunds.com/car-buying/ has some good starting info. You want to read about how the dealer sets their price, how you can figure out much profit they stand to make (and thus what offers they can accept from you), what their negotiating tricks are (read "Confessions of a Car Salesman" and understand how dealers use the misleading math around your loan, monthly payments, interest rate, length of loan, etc to raise the price of the car) and how they use the price of your trade-in in misleading ways. 6. The basic strategy is to know what other similar cars are selling for in the area, test drive several, and then choose your price and stick to it. You call up a dealer and say "I'm interested in test driving this car" then you go for a test drive. When it comes time to talk price, let them know that you are looking at other cars of the exact same year, color, etc and those cars are priced lower. You'll say "let's not talk about the loan or trade-in, let's settle on a price. We want to pay $x." Then there will be hours of theatrics ("let me run that by my manager, I don't think we can possibly go that low but I'll go to bat for you") and you eventually say "ok, we'll leave. Give us a call if you reconsider" and then be prepared to actually leave. Either they'll cave in, or they'll cave in several days later and call you.

(Thanks again, everyone--even most of the answers I didn't mark as best answer contributed significantly.)

I drove my manual Honda Fit (2010) from the Bay Area to Tahoe last week in the snow, and three different drivers agreed that it was fine for a car that gets occasional use in the snow. It doesn't much like accelerating up hills at highway speeds, but other than that it's a great car - for what it's worth, I drove a 2nd generation Prius up the Rockies and it wasn't much better.

If I were in your position, I would look for a late-model Impreza hatchback. The AWD no doubt adds some to the fuel consumption, but it pays back much more in driveability and safety. I've had a Subaru Liberty (sold as Legacy in the US, I think) as my work car for about 4 months (~12,000 km) now and there's no way I'd buy any other brand if I were looking for a new or used car around this size. We are looking at buying a new (personal) car this year and it will be an Impreza. Our work fleet has a number of hybrids and my experience is that, for real driving, the economy isn't all that it's cracked up to be, although I live in a sub-tropical climate so maybe more use of the air-conditioning impacts on that. In fact, for my commute (a combination of 110 km/h highway for 50km or so and stop-go traffic for 15 km or so), the Liberty gets slightly better fuel consumption than a Civic Hybrid used to. I would expect an Impreza to be better again. In the position you are in, where you have a one-off opportunity to set yourself up with a decent car but limited on-going capacity to pay for major maintenance, the idea of a hybrid would scare me. Nobody really knows how long the batteries will last and the only certainly is that they will cost more than you can afford to replace. Environmentally, I'm not convinced that the hybrids of today are that far in front, when you factor in manufacture and disposal of the batteries. In short, take this one-off chance to set yourself up for worry-free driving and play it safe – if you want to save the planet, buy a bike as well.

getawaysticks, there's a substantial chance that a 100-mile/160-km 5-day-a-week RT commute is in my future. I can't say I'm not tempted, but their mileage just doesn't look good to me compared to the other cars I'm looking at, and it doesn't really fit with my overall attempt to reduce my use of energy and so on. :/ When will they make my dream car?! And thanks to various people for the audio input (ahem) so far--it definitely wouldn't be a deal-breaker on a great car (the local guys who speedily put in my cheap-o Target system the morning before we left for Yosemite were great!), but it could be a tie-breaker on two similar ones just to avoid hassle later. Embarrassingly enough, I seriously don't ride with enough other people to have had a sense of how modern systems work.