I am a pilot that flies out of Laconia Airport. I can tell you that getting my pilots license was one of the most enjoyable experiences of my life, and flying is now my favorite hobby. Like anything, there are positives and negatives to getting a pilot's license. I could write a book on the pros/cons, but here's a quick list to get you started:
Pros:
1. The Obvious: It makes getting places faster. Nantucket in about an hour? NYC in about an hour and a half? Niagara Falls in a couple of hours? It sure is nice to get to those places without killing the day traveling.
2. It is exhilarating. The scenery can be wonderful, and the ability to manipulate a vehicle in 3 dimensions is surreal, and an experience that most people will never get to experience.
3. It is intellectual. I found that learning to fly is a never ending experience. The day you get you pilot's license, you are like a kid on a tricycle ... you can ride a bike, but you're a long way from driving a Harley. I personally enjoyed learning as much as I could about flying, so that I could become more proficient, and make better use of my pilot's license.
Cons:
1. It is expensive: First, to get your license, expect to spend somewhere in the neighborhood of $7,000, including plane rental, instructor time, and the invariable little pilot accessories that you'll end up buying at
www.sportys.com . After you have your license, the only way to use it is to either rent a plane, or buy a plane. Either way, expect to spend about $125 +/- per flying hour for a basic, older, Cessna type plane.
2. Training Time: You need some time on your hands to get your license. I believe most people average about 50 hours of flying time. The legal minimum is 40 hours. Also expect about an hour of book/classroom time for each hour of flying time. I did my entire pilot training in about two months. I found that doing more intensive training helped me to remember things from one lesson to the next. Some (if not most) people take a much longer time, and therefore probably have to spend some "extra" hours getting refreshed on what they learned during previous lessons.
3. Proficiency: I could easily call this section a "positive". Once you get your pilot's license, you need to fly enough to keep proficient. For the "nice weather only" type pilot, that might mean flying a minimum of 30 or 40 hours per year. For an "instrument rated" pilot (who can fly in clouds), I think it takes more to stay proficient. I am an instrument rated pilot, and I fly about 150 hours per year, which I feel is sufficient to keep me current in a somewhat complex multi-engine airplane.
4. A Mission: I think that most pilots need a "reason" to keep proficient, so they need a "reason" to fly fairly often. I make good business use of my plane, and that is the majority of my 150 hours. If you don't have a business reason to fly, I think you have to have a place that you and your friends/family go fairly often, like a 2nd home, or some other common travel destination. Of course, there are some people who enjoy the act of flying so much, that they just go off on weekends and "find a place to go", purely for the enjoyment of the flight. Either way, you've got to be thinking that you'll find a way to get in the air at least every couple of weeks, on average. If you can't/won't do that, I think you'll just let your pilots skills fall by the wayside, you won't be able to justify the expense, and you'll stop flying.
5. Plane Availability: There are some pilots that always rent a plane. However, that entails making sure the plane is available, and often precludes taking the plane for an extended period of time. I think that most pilots, that fly enough to stay proficient, find a way to get access to a plane that is more readily available, either through personal ownership or shared ownership. Plane ownership can be more economical than renting if you fly often. If you get into more complex planes, the sky is the limit in terms of cost. It is not uncommon for owners of complex planes to spend $50,000 to $100,000 per year to feed their hobby. Jet jockeys can spend millions per year.
6. Sport Pilot: There is a fairly new pilot license category called "Sport Pilot". In theory, you can get a license in half the time. In my opinion, there is no way that you can be a capable pilot in half the time. You certainly won't be "travel ready" in 20 hours. Also, the Sport Pilot certificate is limited to very small aircraft, with minimal load carrying capabilities. Again, the aircraft is not a travel machine. One advantage to the Sport Pilot certificate is that you do not need a medical certificate. For some people, who might take anti-depressants, or have other relatively minor, but disqualifying, ailments, the Sport Pilot certificate is the only way to get in the air. In my opinion, the Sport Pilot certificate is best suited to those few people who can't get a medical certificate, but love to fly so much, that they fit into the category of those who "just find a place to fly" on weekends. The Sport Pilot certificate is not, in my opinion, a good shortcut to flying a travel machine.
7. Convenience: Private planes are not as reliable as your car, or as commercial airlines. First, they have a lot more mechanical problems than what you would experience with your car. Second, private airplanes are much more susceptible to weather related travel cancellation. I can't tell you how often I say, "I'll have to drive", when I would have preferred to use my plane. Sometimes a plane is VERY convenient. However, when you flew to NYC on Saturday, and you can't fly back on Sunday because of weather, it sure is a pain in the butt.
My recommendation. Spend $100 +/- and go take an introductory flying lesson. I'd recommend that to anyone, even if you don't think you'll want to be a pilot. Even if you don't end up taking lessons, I'll bet it's one of the best $100 you will ever spend. After the flying lesson, if you think you can afford it, and you have the time to invest, take some more lessons. If you get bit by "the bug" (like I did) you'll have done one of the most self rewarding things you will ever do in your life.
Happy flying.