Nubie Question: New or Used for New Pilot?

If I were to take out one of those 20 yr financing plans I could afford up
to $200k. Not saying I want to, just saying I could (and live on soup an
romin noodles for a few years). Okay it would not be that bad but it would
be tighter than I would like. Anyway, if I were to decide to get a plane,
whats the best route new or used? It seems like if I want any type of
saving to justify going with a used aircraft, I have to get something at
least 20 years old. What type of things would I want to consider if buying
something 20 yrs old?

I am looking for something to take me on extended weekend trips to my family
who live around 700 miles away and I would like something that holds 4
adults in some level of comfort for shorter 200 mile trips. Considering my
use is it better to get something older that wont depreciate as much or
something new that will be more reliable and have new avionics/GPS?

I dont plan to do anything for about another year (saving up for down
payment), but I jsut wanted to get an idea on where to focus a majority of
my efforts. Granted, Ill keep all options open but I just dont want to
waste time looking at something thats not right for me.

Thanks,
Pico