The issue is, this engine really RUNS fine. Leaks everywhere, but it idles smooth, doesn't smoke badly (just a bit under heavy revs) - no real FUNCTIONAL issues aside from the carb, which is another story. Compression is great too...
I can reseal/replace what needs replacing for about $500. $800 if I go overboard basically resealing/replacing everything - just not messing with the bottom end. My own time isn't technically free, but if I didn't want to invest labor, I probably shouldn't have bought a 40 year old frankentruck

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As much as I'd love a brand new, worry free engine, a base 350 long block would set me back $1600 (double). Plus I'd also need all of the stuff that doesn't transfer over from the 283 - Harmonic balancer, flywheel, water pump, pulleys, brackets, etc. So at that point, I'm well into the $2000 range.
I guess what it boils down to is - given what I know about this engine, is spending $500-$800 on it really just throwing good money after bad? Because that $1200+ I didn't spend on the new engine could fix a lot of other problems on this truck!
In a perfect world - what I would like to do is reseal this engine, replace what needs replacing, and run it while I tackle the other projects (bodywork, tires, etc.) which, at the rate I'm going, will probably be several years. Then, maybe once the truck is in otherwise top-shape, drop in a crate 350. That said, this is my first project vehicle so I'm learning as I go. If the general consensus among the "pros" here is that I'm wasting my money, I guess I'll just keep saving my pennies for a new engine.