(1) True, a 302 is cheaper to rebuild. However, you're forgetting the cost to swap and get it all working. Whether that cost is your time or cash dollars, it can get expensive quickly. How expensive depends on your skills and capability. I do suppose that the right person could get it done for less, but most people could not. To keep it apples to apples, when a running Y could be found and installed, the 302 is not cheaper even if the Y still needs rings, bearings, and a timing chain.
(2) Y blocks prone to oil leaks?? Many Y blocks are now 48+ years old. Yes, worn out engines leak. 302s suffer the same fate. When they have been rebuilt and sealed correctly, they don't leak.
(3) Overheating?? I guess this could have the same cause as above, 48+ years old. Renew the cooling system and everything is good. A 302 will not magically unclog a radiator, repair rusted vanes on the pump impeller, or fix a generally poor design of the car in regard to cooling.
(4) This seems to be true in the trucks if and only if it is an 80s or newer roller cammed, fuel injected 302. Anything less and it is down on power and economy. Can't speak for the cars, but I think it's safe to assume that they would follow the same trend. So if you choose your 302 wisely, yes it can be better in the economy department, but most are just a waste of time and money. There is a guy on one of the Ford truck sites who is putting one of the later injected 302s into his truck but converted to a carb. It's not done yet, so I have no economy results.
A good, fresh Y just has torque that you can't get from a small block, at least not without a lot of modification. The only way to understand is to drive one. Sadly, most don't have that option, only the aforementioned worn out 48+ year old engines that, understandably, will be dogs, as any worn out (pic your favorite engine, enter here) will be. Plus, they sound a whole lot better.
Lawrenceville, GA