If whenever you start to look at things differently from starting to end and goals, you begin to realize your decisions were either way off or on target....most of the time, way off.
Don't just look at your truck, look at your job, house, even your wife.....lol.
I had a townhouse in the 'burbs of DC. I owned it for 7 yrs. Most first time home owners will make 20% on the sale of their first house in the first 7 yrs. I sold it ('99) for $7k more than I paid for it and that didn't even cover the realtors costs....then within 1.5 yrs (2001), that owner sold it for a gain of $85k and back in 2004, it was worth over $400k. It was a townhouse 18' wide (2 car garage) and 40' deep with a sunken finished basement, 3 bedroom 2full/2half baths. If I held onto it by renting it out for a year, I could have paid half of my current home.
It is always the same thing with additions and mods on your vehicle. Vehicles are a loosing investment to the greatest part. Homes, land, etc are a gaining investment to the most part. Whenever you add/mod a loosing worth, you are at risk to loose greater than its worth. (Meaning, not many others want to purchased a vehicle with your choice of mods.)
I wouldn't look back and take heart on the choices you made. You can take look back and learn from those choices and the end results. And that is hard to do with keeping the original goal in mind.