Been licensed for a while, but the last time I flew was shortly after 9/11.
Some of this may be out of date.
As OM said, it's a slippery slope, and I'm not just talking about airplane upgrades.
There are a couple of ways to go, and each has it's perks.
Sport
Recreational
Private
I would go with the Private Pilots license since you probably want to carry passengers and fly at night over long distances.
There are ratings/endorsments for each additional skill you need... like
Tail dragger
Instrument
Over 200hp
Retractable gear
etc...
If you want drive a plane for money, or to help others make money (LOL!), you need a Comercial license.
Each License, rating, endorcement requires that a certain minimum number of hours of Ground and In-cockpit time be logged. This is a minimum, you continue until you can show minimum proficiency. The test is verbal/practical. You and the tester "chat" for a while. They will ask you questions to find out if you know "WHY" something is, or get you to "THINK THOUGH" a situation. Then you and the tester will climb in a plane and you will demonstrate what you have learned.
You pay for:
Instructor time
Aircraft time
Fuel
Test fees
Materials/books/tools
Anything beyond the Sport license requires a yearly Medical.
I spent around $5,500 in the late 90's to get mine.
Plus:
You get to fly in for $150 pancake breakfasts/burgers.
Your options for taking the Wife out increase exponentially.
Your "reach" for "Day Trips" with the Wife is much further.
A number of Airports have "loaner cars" and all have friendly/helpful people.
You get credit (ground school hours) for attending FAA seminars.
If anyone wonders if there is a Pilot in the room, you will shout "I AM!"
-Ron