OK, after hearing the power dissipation issue, you may want to do that switcher!
One of the big issues is going to be power dissipation in a linear. Lets do the calculations:
Input voltage: 14 (I'll tell you later why you need to protect the input against higher voltages, but this is good for our purposes right now.)
Output voltage: 5V (I'll just calculate nominal. I'm gonna play College Prof, Calculating the maximum is an exercise left for the student.

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You want an output capability of 1.25A. (Note that you may want to allow for more, depending on what you will charge. Many phones pull more than the 500mA spec in the old version of the USB specs. A new version of the USB specs allows for devices that consume up to 1.6A. I believe the iPad uses 1.5A)
So, power dissipated is P = V * I, but the V is the voltage dropped in the regulator.
So; P = (Vin - Vout) * I = (14 - 5 ) * 1.25 = 11.25W Yikes! Without a fan, you're going to need quite a large heat sink, or it will get really hot.
So, another exercise left for the student, is using the Rth j-c (R theta junction to case) from the regulator data sheet, and find out what the Rth of your heat sink is, you can calculate the maximum temp of the die in the regulator based on the power you will dissipate. Be sure to allow for doing this on a hot day, when the device has been sitting in your hot car. Then compare that number to the max die temp given in the data sheet of the regulator. Keep picking bigger heat sinks with smaller Rth until the heat sink gets so large, you dont want it, or you find a die temp that is under the max die temp given in the parameter table for the regulator.
Other concerns that are true no matter what you do:
A car is a brutal electrical environment. If you are going to plug this into a cigarette lighter socket, be sure to choose a fused plug. Then be aware that you should likely choose a TVS device to clamp the maximum voltage your circuit can see. Transient voltage spikes of 60V can occur in a car during what is termed "load-dump". Go to some of the TVS manufacturer websites and you'll find some good papers on how to choose a device, and the kind of voltage spikes you may see in an auto, and what parameters to choose for the TVS.
To answer your question about the current sense. On the output side, you will want to use a fairly small valued resistor, in the low side current return path. You will want it to be a small value, or it will seriously reduce your output voltage. Remember that any voltage dropped across that resistor will be voltage your USB device being charged doesn't get. So, you might want to keep the resistor to say 100mOhms, or 0.1 Ohms. At 1.25A, that will be a voltage across the resistor of 125mV. You then will use an Op-amp to gain that voltage up, so that the voltage is close to the maximum input voltage for the A/D your micro has. For example if your micro runs off 5V, and full scale on the A/D is 5V, Gain = 5V / 125mV = 40. Note that you may want to do a bit less than that, so you could detect if a device is drawing current higher than what you planned for. The concerns on the input side are quite similar.
Show us you're first pass at a schematic, and I'm sure you'll get lots of feedback. Engineers are good at telling others what they are doing wrong. LOL
Seriously, this is a good project for someone new. I think you can have success.