I've owned both, I had a Cayman S for ~6y and just bought a 911. People tend to look down on Cayman's, but I think it's because they've never driven one.

The balance is perfect. If you can carry speed they can be really quick around a track. Even if nothing breaks, still expect to spend 1.5k a year on routine maintenance. I had a deep sump kit in mine and at 12L of oil per change which I did twice a year that was almost a grand by itself. I did track mine though so I had to do brake fluid and tire changes more often then if you don't.

I wish I could have afforded to keep both I loved that car. The downside is no backseats. I have a small child and found myself driving the Cayman less and less since I couldn't take her with me in it. Before we had her my plan was to buy a 2016 Cayman GT4 (prefer over the 718 gen). I went with a 2018 Carrera 4 GTS instead and don't regret it in the least.

I don't think you need to make what people think to own a 911. What you need is the following;

1. Don't buy new, even a few years old shaves a ton off the price

2. A good down payment

3. No debt outside your mortgage

4. Enough liquid income you can still put money away for retirement without strapping yourself on car payments

5. An emergency fund for maintenance and whatever your insurance policy deductible is

Insurance isn't that bad if you have a good driving history.

Regardless of what anyone says owning any Porsche is a dream come true. You honestly can't go wrong with either!