Nubie Question: New or Used for New Pilot?

Among new airplanes you would have a choice of the Cessna 172S or a Diamond.
These planes will fit your mission profile quite well. The Diamond has a
wider cockpit than the Cessna.

Airplanes depreciate quite a lot the first three to five years then
gradually start to increase in value. Exceptions would be airplanes like the
Cirrus SR22 which has a severely restricted airframe life; some of these
planes are already approaching mandatory retirement.

Probably the best deals out there are used late model Cessna 182s.
Trade-a-Plane shows several of these as low as $170,000. The 1998 and 1999
model years were very good airplanes. There are also some used Cirrus SR20s
that are less than $200K and they still have a lot of life in them.

You could take an old airplane and re-paint it, put new interior and
avionics in it, a new engine, and guess what? It is still an old airplane!
It will never have all the safety features and capability of the newer ones.
The new Cessnas may have the same model designations as the older ones, for
example, but they might as well be different types. They are faster, more
fuel efficient, and far more comfortable. Everything from fuel systems to
avionics to engines has changed. Even the supposedly draggy airframe got a
thorough going-over.

Still, for the down payment that you put on one of these shiny suckers you
could buy an ancient 172 that will still fit your mission profile and you
won't have any monthly payments at all. You might even be able to afford to
fly the thing now and then. You could lose your job, but you won't have to
give up your airplane in order to be able to eat. Personally, I find far
more comfort and safety in staying out of debt than in having the latest new
thing. I would not buy an airplane that I could not pay cash for.