Location, location, location. Height is might. Elevation is propagation. The biggest advantage of a repeater is that they are usually very high. Most HTs (handheld transceivers) -- yes, including Baofengs -- are capable of communicating by simplex to another radio 20 miles away, but the probability that two people standing at ground level will have a straight line-of-sight shot to one another is very low. I've once talked HT-to-HT approximately 22 miles. We were both on elevated terrain features and even so, the signal was weak and scratchy. Repeaters are another beast entirely, due largely to the aforementioned elevation. This morning, I participated in a net hosted on a repeater 20+ miles away with a Baofeng UV-5R Mini using 5 watts and the stock antenna. With a 5-watt GMRS HT, I regularly use a GMRS repeater 27 miles from my house...but my house is on one of the highest points for miles around and both repeater antennas are ~300 feet above ground level.
What I'm saying is that it's technically possible for you and your buddy to talk to one another 20 miles apart with Baofeng handheld radios...but it's probably not going to happen in the real world. If you are both appropriately licensed, a whole new world opens up with repeaters. It's not at all unlikely you can communicate through the repeater, although there are a few caveats. The fact that you can hear a repeater doesn't necessarily mean it can hear you. A GMRS repeater is typically 50 watts, and a ham repeater is usually in the 50-70 watts range, but some of them output much more, sometimes 200-300 watts. That means the signal can sometimes "power through" some minor impediments like trees and buildings when your 5-10 watt HT cannot. Power isn't as important as a lot of people think, but it isn't inconsequential either.
Bottom line...get licenses and use repeaters. There may be GMRS repeaters in your area. If so, that's a good option for getting started. No test is required for a GMRS license -- just pay the FCC $35 and you get a license good for 10 years, and all your immediate family can use it. I've known people who got a GMRS license in 2-3 days, although it's usually more like a week. Then study for an amateur license. You have to pass a test, but it isn't too difficult. It's also $35 for 10 years. There are a lot more ham repeaters than GMRS repeaters, and they often have the most advantageous locations. Since you already have a radio, I recommend you don't buy another one until you've gotten a license and played around a bit. You might discover you aren't as interested as you thought you were and you don't want to be stuck with hundreds of dollars of equipment. The little Baofeng is a perfectly serviceable radio as long as you have reasonable expectations.
