Using your example there are a lot of differences between a 59' and a 09' 172. There are so many when you think about it it's hard to list.
Advantages 2009:
24V better grounding, wiring, etc.
Airbags and sholder harness standard
G1000 w/ GFC700 autopilot
Corrosion protection from the factory
Fuel Injected IO360 at 180HP
Better dash lights
Better seats
NO seat track AD or any other significant AD
No hidden damage, engine corrosion, rigging problem, etc.
Whatever else I missed
Advantages 1959:
Purchase price, maybe see below.
Look at the Van Bortel deal on a new 172:
http://www.vanbortel.com/pdfs/UAD_PC.pdf
You can basically dry lease a 172 and put 100 hours on it in 6 months for $50 per hour!!!
Now you don't have a project sitting in the shop for a year, you can just go fly a brand new airplane. You have a full warranty. You can give it back vs. giving it away if you want something else.
I just don't see it, unless perhaps you were an A&P that loved the classics and could do much of the labor.