Hi everyone,
I’m 23, a law student in Eastern Europe, and I run my own small business. My long-term dream car is a Porsche 911, but I don’t want to destroy my business cashflow with an expensive lease too early.
I don’t get financial help from my parents, so everything I buy has to come from my own work. I also have around $22–23k invested in ETFs, so I’m not trying to spend every cent I have on a car. At the same time, I’m young once, I work hard, and I’d like to have something enjoyable in life instead of only saving and waiting forever.
I’ve been running my business for about four years now, and honestly, I haven’t really bought myself anything special during that time. I’ve mostly reinvested, worked, studied, and tried to be responsible. So part of me sees this car as a reward for the last few years of work — not something financially stupid, but something that lets me enjoy life a bit. Waiting another 2, 3, 4, or 5 years for a “proper” 911 feels a little depressing. I don’t think I need the newest 911 just to enjoy cars, summer, and taking a girl on a nice date.
I already have a sensible daily car. It’s not exciting, but it does the job. That’s why I’m not trying to buy one car for everything. I’m looking for a first “special” car — something for summer, weekends, dates, university life, and just enjoying cars while I’m still young.
I was looking at newer cars like a BMW M440i / M2 / Porsche 718, but the monthly costs would probably be too high for where I am right now. I could technically make it work, but I don’t want the car to become financial pressure.
On paper, I could probably get approved for financing/leasing on something like a Porsche 911 991. But realistically, I don’t want to put 70–90% of my monthly income into a car lease and then be afraid to actually drive it. If one unexpected repair meant I’d have to take another loan, then I don’t think I truly “afford” that car yet.
I also thought about a Porsche Macan, because it’s still a Porsche, or an older Boxster, but I’m worried that would be buying too much “for the badge” rather than because it truly fits what I want.
To be clear: I do not want to buy a crashed 991 or any newer 911 with multiple accidents just because it has the right badge. I’ve seen how “budget repairs” are often done, and I don’t want to end up with a badly repaired car that only looks good in photos.
So now I’m mainly torn between two realistic options:
- Mercedes SL R107 A classic Mercedes convertible, probably bought for cash. I like the old-money / timeless look, the summer vibe, and the fact that it feels stylish without trying too hard. It would be more of a weekend/summer/date/university car, not a daily.
- Porsche 911 996 A real 911, older and more attainable than newer generations. I know it has its own risks, especially if it has high mileage or poor maintenance history, but it is still a 911 and closer to my actual dream car.
The appeal of the SL R107:
- classic Mercedes convertible
- timeless/old-money look
- stylish for summer and university life
- cheaper entry price than a clean 911
- keeps more cash in my business
- feels special without pretending I can afford a perfect 911 yet
The appeal of the 996:
- it is a real 911
- closer to my dream car
- probably more exciting to drive
- more recognizable as a sports car
- may hold emotional value better for me personally
My concerns with the R107:
- rust
- old-car reliability
- soft top / hardtop condition
- parts and maintenance
- buying something cheap that becomes expensive quickly
My concerns with the 996:
- high mileage
- maintenance history
- engine-related risks
- buying the cheapest 911 and regretting it
- potentially higher running costs than the Mercedes
I’m not looking for a perfect daily driver. I want a first “special” car that feels stylish and enjoyable without destroying my finances.
What would you choose in my situation: Mercedes SL R107 or Porsche 911 996? And why?
Also, are there any other cars in this general price range that you would recommend for this purpose- something special, stylish, fun for summer/weekends, and not financially reckless?
Any advice from people who have owned an R107, 996, older Boxster, or similar cars would be appreciated.