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3-4 years convertible ownership minimizing outlay

I'm looking to get a sporty convertible porsche for 3-4 years and somewhat minimizing my outlay. I'm looking to spend 30-40K, then sell it in 3-4 years, and somewhat minimizing the buy-sell+maintenance outlay for the 3-4 year period, while still having a car i love.
My first thought was a CPO boxster S, looks like i could get a 2008-2009 for just under 40K. Still significant depreciation, losing the CPO magic, but i'm somewhat secure that i'm not getting a lemon.
Then i saw a 2004 cabrio turbo, asking 42K. Maintenance will be higher, of course, but i'd imagine depreciation is already largely done assuming i take good care of it and don't put on a ton of miles. I grew up thinking if i made it big-time i'd have a turbo, and if i was a famous rock star it's be convertible, and, well, there it is... But is it going to eat up >5K a year in service, brakes, tires?
Middle of the road, i'm seeing 2006 or so carbio s's for around 40K too, slotting in between the above cars, i guess.
Thoughts?
My first thought was a CPO boxster S, looks like i could get a 2008-2009 for just under 40K. Still significant depreciation, losing the CPO magic, but i'm somewhat secure that i'm not getting a lemon.
Then i saw a 2004 cabrio turbo, asking 42K. Maintenance will be higher, of course, but i'd imagine depreciation is already largely done assuming i take good care of it and don't put on a ton of miles. I grew up thinking if i made it big-time i'd have a turbo, and if i was a famous rock star it's be convertible, and, well, there it is... But is it going to eat up >5K a year in service, brakes, tires?
Middle of the road, i'm seeing 2006 or so carbio s's for around 40K too, slotting in between the above cars, i guess.
Thoughts?
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That said, I'll get some other folks to review your request and chime in with their opinion.
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2015 Subaru Outback 3.6R / 2014 MINI Countryman S ALL4
The trick to buying a used Porsche turbo successfully is based on what you do BEFORE you buy it. 1) you hook up with a reliable, qualified independent Porsche repair shop---not a GERMAN repair shop, but a PORSCHE specialist. 2) you pay for a thorough pre-purchase inspection for $350 bucks. Best money you ever spent.
The Turbo is the best 996 you can buy, period, hands down, even if it costs you more money to own. Buy the best car you can afford. The cheapest Porsche usually ends up being the most expensive one.
The 996 in general does not have a good reputation among the general public, so don't expect resale value to go anywhere but down. And the Boxster resale value is even worse because they are a dime a dozen. But "those in the know" know that the 996 Turbo is a different animal and a wonderful car to own.
Do you think even a 2008-2009 boxster has significant chances of engine failures? That's unfortunate news. I saw a pretty nice 2008 rs60 spyder.
I drove a boxster S and that is a fine car. Also drove a '07 911S cab which was, i think ruined by its tiptronic transmission.
I did drive the 911T ( manual, cab ), and it was really wonderful. What a vehicle! The main thing that worries me is the dealer gave me a coupon for a free first service, *up to $2,500*. That had the opposite effect from what i think they intended. Your budget of $200 a month--is that assuming i actually drive the thing, say, putting on 12K a year?
I think you'll laugh at me shifty, but i drove a c6 vette, since the dealer with the 911S had one sitting right there. I drove it to prove the 911 porsche was worth the extra money, and came away feeling the opposite. I still like the 911T better, but i'm guestimating the vette will be 1/2 the ownership costs or less, so i'm thinking that through.
Thank you for the advice and help!
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