Nubie Question: New or Used for New Pilot?

It depends a lot on how the previous owner and his/her A&P treated
maintenance issues. Catch-up is very expensive. It also depends on
your attitude. Retractable gear can add significantly to maintenance
cost if the owner is very particular because the cost of failure is so
high.

Example: gear strut shows leakage. One owner will have the seals
replaced immediately, another will let it go until it's flat, another
will put on the list for the next annual. Multiply this by 1000
individual parts.

Review the annual logs. On an older aircraft (5 years) it should
show lots of nitty-gritty fixes - seals, hinges, wires, etc.