1996 engine swap into 1966 thoughts

[ChevyTruckGuy]

I have a 1996 silverado 1500 with new rebuilt auto trans, all stock including the 5.7 Vortec. Drives perfectly. Owned it for 18 years but should downsize on some of my vehicles. Its a long bed Single Cab.

I also have my 1966 that I went through with my brothers help about 10 years ago, it has a 350 three speed auto and a 4 barrel double pumper holly. It started puffing rich white smokey exhaust about 5 years ago so I parked it unfortunately. Owned it since '98. Previous owner used it as a track truck so it sorta has some decent power, I really like it.

When I first purchased the 1996 Silverado mid 2000's I thought about putting that engine and maybe trans into the '66. Today the 1996 Silverado is for sale and i'm so sick of all the low baller time wasters. Then it hit me, my idea from before about placing the 1996 Vortec into the 1966.

Whats involved in doing so? Is it an economical swap? I don't think the Vortec is a LS or is it? I like it regardless. I like the idea of fuel injection for the 66 and its a proven power train. I'm not very mechanical, i'm a wood worker.

Is that a bad idea, I have 9 vehicles and really should downsize, honestly I have half on non ops because the auto insurance is killing me here in Cali for the past 3 years.

Maybe it would be better to take a lowball offer on the '96 and buy a fuel injection kit or something for the '66? I don't know, Im only asking 3k for the 96 obs but spent 4k on a trans rebuild 8k miles ago. Its pretty clean but high milage and its a long box. I have new trucks too but thought about daily driving the 96 instead.

Any thoughts or advice would be appreciated, This guy really upset me today, even after negotiating a price for the '96 and me driving it to his house to show it to him (he's a local with no transportation), he still proceeded to try to get an additional 30% off the price. i'll let it sit before that happens or just use it as a donor for the '66. thank you guys... Sorry for the long post,just frustrated.