You may also take into consideration that the 355 is an "engine out" belt service done every 3-4 years. This is around $7-10K depending on who you know and if they're a reputable shop.
I agree with some other posts. Save up for a 360 Modena or if you can, the F430. both are cheaper in service (engine in) and more reliable.
Also, do a PPI before you buy anything and make sure all the services are up to date (with records). Consider a pre-owned exotic car warranty as well - just to be on the safe side.
When something breaks on a Ferrari, it's not cheap
Insurance isn't too bad if you go Hagerty or Grundy car insurance for a weekend toy or collectable
Good luck with whatever you choose :-)