Here's my take:
1) depending where you live certain things are harder to find than others - southern cars dried out runber/plastic/interior, northern cars rust.
2) the ask is 3500. Maybe he takes 3. Either way, these days 3500 doesn't buy you much. You could get a 240k mile honda for the same price, ad both will keep breaking due to age
3) see above. The newest of these cars are pushing 32 years old. They will break, stuff will wear out, replacement bits will be a pita to find.
Depending on your budget, for insurance and future proposed it's always better to start with a special trim level model. Herte that means bumping it up into the 8k range for a similar 443 if you're going to invest much in it.
If you just think the cutlass looks cool, want something to tinker with on the weekend and putt around in, maybe this is for you.