355 vs 360

I would think that getting into a 355 would be great for someone who wants to immerse into maintenance as part of their ownership experience. I have done this with my 360 and it is very rewarding to wrench on these cars. Only recently have I had to kick it into the dealer as my life got busy but I still get hands on and accept it as part of my stewardship. YMMV

 

It's called supply and demand. If there are a lot of cars available and nobody wants them, the price goes down. Conversely, If there are fewer cars and more buyers, the price goes up.

I think it comes down to nostalgia, looks, and sound.

Performance wise they are both pretty old. As good as my 348 Challenge, F40 and CS were, neither one would know which direction my McLaren 570S went. The game has moved on.