Wow I replied to this thread years ago and I just bought my first NSX last August (2016).
Based on your response compared to your first response in 2014, seems like you still have some more thinking, planning or researching to do as you are still skeptical about the "worth" of buying an old car vs. new (different) car. :wink:
It really depends on what you think is worth buying and driving once or twice a week as a fun weekend car. The maintenance and headache depends on the condition of the vehicle that you purchase. If you buy a good example then there will be less to no maintenance or headache. Whereas if you buy a poor example, then there may be some to a lot of maintenance and headache involved. With a $55K budget, you should be able to find a good one with up to date maintenances and still have money to blow on mods should you consider an earlier model (91-96). If you do buy a 91-92 make sure it's not in snapring or if it is, it has been dealt with by previous owner(s). I wanted a more raw driving experience so I went with a '91.
You should probably find one to test-drive or sit in to see if you like it. I considered a Cayman, s2000, BRZ/FRS, mustang, Miata, WRX, and 370z when I thought about buying.
Good luck and keep us posted! :biggrin: