Throwing the idea around for another square body

[chevymotocross]

Sitting here, before I go out for some more festivities I have been thinking for a bit now of another square body. I currently have a nice 87 silverado swb 2wd. It is strictly a daily driver. 305, added a sway bar, true duals, k&n drop in, soon a 2/4 lowering kit, and that is it. It gets good gas mileage, and has working a/c and power accessories. Is it slow.... yes, but it is a daily commuter and very reliable.

I was tossing the idea around now, for a few years, for a harley. After a few buddies getting hurt on street bikes, one even killed, I have decided not to get one. I figured I will not have many people to ride with, to make the $10,000+ purchase of a harley enjoyable. I got my motocross bikes to make motorcycle riding fun

So, for this new year, I want to get a new toy. I have my 87 daily driver, so if I get another square body, it will be built with one thing in mind.... going fast!

My dad says I should instead invest in a newer truck and sell the 87 since he thinks it is getting too old to be a daily driver. I tend to disagree but the 305 does have some miles on it, but the truck runs excellent! He thinks I should get a newer 99+ swb with the 4.8 or 5.3. They are nice trucks indeed, I like the bodystyle. I have seen a few videos of those trucks with cam, chip, exhaust, and they are fast, but there is something about a 73-87 that are timeless!

In CT, anything 25+ years old is emissions exempt, which is great. Engine choices seem endless with these trucks. I want a package that is streetable (I'm not going to race it). Something that delivers good torque and good highend, so I am thinking small block. What are the better engine choices? Built 350? 383? Carb only, I am not doing any electronic tuning here (I have an 87 for that if I wanted to).

I always liked the 73-80 trucks. I have an 87 now, with the square lights, so an older round light truck would be cool to have. But if I found a deal on an 81+, I would snag it.

I got extremely lucky with the finding of my 87. To find an 87, with silverado package, swb, 2wd, with minimal rust, in CT, for under $3000 is a dream in New England. Unfortunately, 73-80 trucks here are almost extinct!

So anyways, do you think I should go for another square body, or should I listen to the advice of my father about getting a 99+ truck which I can cam, chip, and do lots of bolt ons, and have a fast truck, and daily driver, in one package?