1988 SS with cracked block
 

Hello ALL - Let me start by saying I am not educated in engines or the ins and outs of tuning them. I am looking for feedback or suggestions. I came across a 1988 SS which was thought to have blown freeze plugs. We got it running and she drives. Once up in the air, the mechanic advised that is has a cracked block. I am now torn on whether to replace with another 305 or increase the engine to something bigger, that will still be compatible with the existing transmission. I do realize that whichever direction I go, this will no longer be a matching numbers car, which I'm not sure what impact that will have on future resale. Any advice?

You wont have many issues if you're switching to a similar year engine. Some minor changes would be needed if the engine is newer or older than 1978 as the oil dipstick changed positions a few times and some other parts changed . As for resale value and the original engine I wouldn't be too concerned , but if you were keep the old engine .