Portable Air Compressors are definitely worth $10-$30. Many Gas Stations will charge for using Air Pumps. If you are like most people, I assume you don't carry quarters. (Definitely not enough to pump up your tires!) I also assume you hardly check how much Air is in your tires too. I'm I right? Yeah, most likely! It's just to inconvenient to worry about!
If your tires are only a few psi low, your handling will be different. Handling in wet conditions will be even worse! A tire will lose .5 psi-1 psi every month of regular driving. Every 10*F change in Temperature will make your tires lose about 1 psi (usually happens when it gets colder.)
A Portable Air Compressor you keep in your trunk will not only save you the hassle, but time and money as well. Your tires will last a lot longer if you keep them properly inflated to the correct pressure. The Fuel Efficiency of your car will also be much better with properly inflated Tires. If you aren't sure about the correct pressure, check inside the door or around the opening. Don't follow what it says on the sidewall of your tires!
You can find Portable Air Compressors in big-box stores or a local Autoparts Stores. Buy a Portable Air Compressor! Trust me, you won't regret it!
Pictured below is my Portable Air Compressor. I bought it at Target for $20, and it's served my family and I well. I've used it on all of the cars we have, including many people's cars who needed some Air when they've stopped by. I'll always have one handy!