OK, I read all the of the other responses and I still like mine the best. And that is what this thread is all about, you asked for opinions, and you received many. What I submitted, works best for me and my situation.
You are very fortunate, you have had a lot of good input posted here that should help you come to a logical decision that will be best for you and your family.
In my younger days, I have done a lot. Rebuilt a couple motors, swapped a 6 for a V8, took out a 3 speed and put in a 4 speed etc. I hated car payments, so I only bought what I could pay for with cash. I was programmed early on that a vehicle is your worse investment. So I stuck with cheap in-expensive vehicles that I maintained and kept running on the cheap. That saved me a lot of money early on that I was able to use for things like remodeling my first house, building a garage, etc.
It is true, that if you buy a new vehicle and sell it within a couple years, you will most likely take a big loss. However, if you buy new, and keep it for 6 or more years it starts to go the other way. It is still an overall loss, as most vehicles are, but it does tend to average out with time.
NOW LISTEN CLOSELY!! I said keep for 6 or more years, and not pay for in 6 or more years. A wise man once told me, that if you have to finance a vehicle for more than 3 years, you cannot afford the vehicle.
In my situation, I drive 20,000 or more miles a year. I must drive the interstate to work daily in rush hour traffic, (usually at 65-70 mph or more). In the summer I pull a camper that weighs 5,000 lbs empty, (before the bikes, canoe, 40 gallons of water, and the rest of the gear). Summers in Nebraska can be brutal, routinely having a lot of days that top 90 degrees or more.
When I get in my truck, I need to get from point A to point B period. It has to always start, and it has to get me there. After getting home from work, quite often I will head off again taking or picking up kids. Although I live in the city, we chose to build our home in an area that offers great privacy (and room for Big Bolts) but lacks the best of city services. I am one of a few in this city that really needs 4 wheel drive in the winter. As my truck is our only vehicle with 4 wheel drive, it has to always be ready to go.
I really love the old Chevy trucks, but they are just not pratical (as an everyday driver) for my lifestyle. After about a 15 year span of not owning an old one, I now own 2, and I am very anxious to get started tinkering again. These will be used as weekend and after work drivers. Especially, now that my kids are getting older.
One good thing in your favor, is that you are considering a vehicle, that should be able to handle the interstate speeds and rush hour traffic OK. I had a '63 with a 283 4 speed that worked well in my earlier days, so you could very well have the same luck.
Athough another thing to consider is, that it is just as hard to restore a vehicle that you need to drive daily, as it is to live in a house with your family, that is in the middle of a major remodeling.
And last but not least, if your goal is to have a cherry Stovebolt, it will be hard to keep it that way, if you drive it everyday.
In my case,I just want to get mine running and driving well, and looking respectable, so I can have a little fun driving them, and maybe turn a few heads at the same time.