Never too late
I should have posted something to this thread a long time ago.
At 62 years old and the son of an auto mechanic, I've had a love affair with cars for a long time also. I don't that any pictures of the cars I had years ago, so I'll post a few "representative" pictures of some of my toys.
When I was a teen, my older brother had a '55 Chevy street rod that I got to drive. When I was in college, he bought an R/T Charger and handed me the keys to the '55 for a few months while he decided what to do with it.
It was a turquoise and white B210 2-dr coupe. Similar to this one:

It had a ~375 hp 327 engine, 4-speed, 4:10 Detroit lockers and traction bars. Lot of fun in a straight line but lousy brakes and would not turn.
My senior year in college I bought a car with my own money - a '69 R/T Charger similar to this one:

Basic 440 auto car. Mine had the brown vinyl roof. It started out with 3.23 gears but I swapped them for 3.90 gears. Also added a 6-pack camshaft to the engine.
Once in the Air Force, I found a '69 Road Runner for sale and bought it. It looked like this:

426 HEMI auto, bench seat, column shift, 3:54 Dana 60 gears. 13.7 in the quarter with street tires and through the mufflers. 12.2 with the headers open and slicks installed. Radar clocked at 162 MPH by a state trooper that was an old HS buddy. Kept this car for almost 12 years.
In the mid '80s, I bought a Grand National Buick Regal like this one:

An '85 non-intercooled car. I added ram air and changed the computer chip to get 17 pounds of boost. Not as fast as the HEMI but it had AC and I could listen to the radio with the engine running.
As the big 40 got close, it was time for a new car - a sports car. Never really considered them until then. A Corvette was my ride of choice. Bought a '92 Vette. Here's a picture my wife had done for me:

It was just white originally but my '96 I thought the GS scheme looked good and had my car striped and hashed. Added ZR1 wheels and GS flares later. Kept this car for 14 years.
Along the way, I married a girl that liked fast cars also and she owned a Corvette also - a basic white '93 but by the time we were married, she had traded up to a '98 Vette. So, we had 2 Vettes in the garage for many years.
My wife traded the '98 and bought a '96 CE LT4 Z51 Vette while I was still driving the one above. After she got the '96, I had to do something to make mine faster - I was tired of getting beat by her. So, the engine got a rebuild with LT4 and Hot Cam parts. About that time, we decided to replace her '96 with a 50th Annie Vette convertible.
The family car was a Buick Regal GS at the time the CTS V1 came out and I began talking about getting one of them. At first my wife wasn't that hot on the idea then she noticed an ad in the paper for an '04 V for just under $40G and I took a look at it that afternoon. Signed the papers and gave the dealer the GS that same day. Drove "DARTH V" home.

Kept this car for almost 7 years.
In '05, I finally replaced by '92 with an '06 Orange coupe:

This is a paddle shift auto. Turns out that I wasn't having as much fun driving this as I had with a stick, so in '07, I told my wife that I was going to get a new Vette and sell the orange one. A friend really wanted my wife's 50th Annie car and my wife liked this car. So, we sold her car and I bought this '08 Vert:

Comp Gray wheels, gray roof, titanium seats, LS3. Nice ride.
I had considered replacing the V1 with a V2 when they came out but there was one problem with the V2 - no fold down rear seats like the V1. I could not get our mountain bikes in the V2 sedan. In 2010, GM hinted that there might be a V Wagon and then it became clear that a V Wagon would exist. I talked with my Cadillac sales manager and the Cadillac regional rep.