Help: What Should My Next Project Truck Be?

So, here's my story. By the summertime I am hoping to have another new truck to go to shows with. Preferably a Chevy. Friends on the Autolog say that I have 2 Blazers and that I should try an S10 pickup. That is fine, but I don't know if I should go with the first generation S10; up to the year 1993. Or if I should go past that and get a second generation S10. I don't really like the second gen, so maybe it would be something different for me. I love the S10 Blazers, but I already have had 2 and should try something different I guess. A GMC Sonoma would be fine too, same thing as the S10.
But... something that is REALLY catching my eyes lately are those Chevy Colorados and GMC Canyons. I don't know what year they started, 2005? And I don't know if they are still making them up to 2009 and on? If someone could help me with those questions, thank you. Also I do not believe that the Colorado Xtreme is made anymore, I think they ended. I would LOVE one of those! But the regular Colorados are fine. I am going to start researching them more. They're hott! The second style Colorado is the one I'm talking about, I think there was a first style that didn't really do it for me. But these new Colorados/Canyons are really HOTT! Especially when they're all customized. I would make a show truck out of one. But... knowing me. I want to put a V8 in it, maybe just the LSI motor, but a V8 you know? Something to beef up the motor! I haven't seen it on the Autolog yet I don't think... but I want to make a V8 Colorado!
Where am I going to get the money you ask? I have found what some call a "barn find"... in my own Grandparent's barn! It's been there ever since I was born, and before that. I remember playing next to it in the sand. The big green thing, just sitting there was an inch of dust on it. A dark green 1940 Ford Tudor. When my boyfriend and I went up there my Grampa apparently said that it had the original transmission and the original motor. When I asked my Dad about it, several months later, he said that it didn't have the original tranny or motor. But anyhow, my boyfriend had asked a friend of his, who buys and sells antique and classic vehicles about the Tudor. He said that, if the car was in the condition that Billy said it was... we would get $40,000.00 if we sold it to him!!! Yes, of course that needed three exclamation points at the end of it! With this 40 we could finish my black Blazer, put the Whipple on the Mustang and finish that, and... buy my Colorado, which doesn't have to be the newest year of them, customize it, put a V8 in it, and still have $10,000.00 left over for a down payment on our new house in June! Well, that was the plan Billy had, but I don't know if it will work. I am calling my Grandparents today to talk to the about the Tudor. My Mom said that my Grampa has been trying to get rid of it for years! Why didn't I even think of that car?! Will keep you updated on the Tudor!

- Jenn.