What Pickup Truck Should I Get for My First Car?

Just wondering what I need to look for in a truck when I go look at them with my parents. Trying to buy something under $4,000. I like the third generation Chevys (73-87.) I'm also a fan of late 1990s, early 2000s Fords. Trying to figure out what years where some of the trucks have the same problems (Example: Almost every 2003 Ford Crown Victoria has a transmission problem where it needs to be replaced.) Now since the trucks I'm looking at are old, any problems that could've existed coming out of the factory may have already been taken care of by previous owners. I live in New England, and we get terrible snow storms here sometimes, so I was trying to decide between 2WD and 4WD. I'm also concered with insurance, so if you guys could tell me what in a truck increases/decreases insurance costs (Year? 4WDvs2WD? Size?)

How do i know what year my MG is?

I have a 1954 MG TD roadster "replica" not "kit" handed down to me by my grandmother. How do I find out it's actual build year? The title states it's an original TD. It has a 4 cyl ford engine in it. So I know it's not a 50's build.