Those are fair points. But keep in mind also, the 305 has low KM as well. So the block, metal wise might be able to take a beating, more than a used 350 with high mileage.Right now there are some very good reasons people haven't mentioned for you to think about another direction... and it's all about the long term.
Rebuilding a motor isnt cheap... at least not done right. You're probably looking at an easy $500-1000 or more on the low end by the time you've torn down, hot tanked, honed/bored, bought new parts etc.
Considerations
1) going to roller cam setup - flat tappet cams require lots of extra diligence as they keep reformumating oils, which they did yet again recently. With a roller you don't need to worry about the lack of metals (zinc etc) in modern oils and pricey additives.
2) building an e85 friendly motor. Let's face it, war has been declared on the ICE. Maybe you don't have longterm plans on the car. But if you do, its time to invest wisely for the future. My bet is you see ethanol content raised again with the idea being EV or e85 hybrids. In a carb motor, e85 is about 25-30% less energy than regular gas and needs to be planned for accordingly- both fuel volume and all you various rubber/plastic parts and seals from tank forward.
3) if the idea is to have the correct motor... but you swap out the original heads, carb, ignition system, etc... it does t really count as numbers matching motor, just original block. Beyond displacement, tere are benefits to the 1pc rear main seal, to getting a motor with roller cam already in place, serpentine setup, all down to even running a slightly reworked l31 motor without rebuilding it or some such similar option.
The idea isn't necessarily kill the 305s... it's more a case where people new to the hobby and type of cars may not see the long game, and the cost vs benefit. Replacing a 305 doesn't have to mean an ls swap. Theres many other acceptable options to think about.
If you are set on doing it, you'll wind up with better quality parts overall if you pick components individually. The "kits" are basically just the cheapest Chinese junk thrown in a box and marked up in price for the uninitiated when you're ordering for a smog era 305.
I'd just hate to waste something, that still has potential. And also, getting a 350 delivered to where I am in the country, would be a challenge. I have no access to a pickup, or an engine hoist. My friend has a block and tackle, and thats it.
I have to tow the Pontiac to his house, via CAA for him to do the work.
$500-$1000 seems unreasonable for sure, but keep in mind in comparison I can't afford a $4000 crate motor either. I'm on disability, and my goal here is to get the vehicle back up and running.