This sounds like quite a bit of work, both time and money will be flying out the window very quickly. Not that it can't be done but you have to look at you and your dad as far as ability, time available, place to work, tools you have etc. You can't drive for two years so there is no rush and if your dad has plenty of time to help you, I would say it's a good learning experience as well as time with your dad. I remember some really great times working on cars over the years with my dad when I was younger.
The flip side of that is you will sink a lot of time and money in a badly rusted car and it will always need more work than you think as you get farther in. Many of us here have replaced almost a full cars worth of sheet metal and have no problem doing it and some will only buy an already restored car just to enjoy driving it. Personal ability and preference really make a big difference.
A piece of personal advice, this should be fun for you or a learning experience or something to do with your dad or hopefully all of the above. Make sure that it is before taking on a project this big.
We are all looking forward to pics too I am sure once you get them up so we can better see what you are working with.
As far as the poll, I always vote for doing it yourself.
1964-1/2 Mustang 260 Conv, 1966 Mustang 289 Coupe, both projects
2001 F-150 Lariat for daily use.