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Buying a Roadster

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Hi Everyone,
In December, I took delivery of my 2017 Model X and am absolutely in love with the car. I recently also put money towards reserving a Model 3. I am thinking of buying a roadster as well. I would appreciate some guidance around the purchasing of it.
- Where should I look for roadsters for sale?
- Any particular year models I should stay away from?
- What is the approximate price I should expect to pay?
- Should I even think about buying a roaster, being that it cannot be charged at SuperChargers? What are the charging options for a roadster when on a road trip?

Thanks
 
Whether buying a Roadster is right for you depends on why you want one, and what you want to do with it. While they technically can be done, long trips in a Roadster may not be the best use for the car, for example.

With available adapters, the car can be charged from nearly any wall plug on the planet, and from both the common J1772 Level 2 charging found around town, and the Tesla Destination charging found at many hotels resorts. So, if you can get somewhere, and that somewhere has some sort of charging, you can probably be fine. But do your homework with tools such as Plugshare, as Level 2 charging is considered by many organizations as an opportunistic perk - nice to offer, but not guaranteed - and are often broken, occupied by gas cars (with no incentive to have them removed), or overly subscribed and hardly ever available upon arrival. Also remember that it will take some time to charge. Usually not a problem if it's overnight, but it can be a significant issue if you want to go further than one charge will take you. Level 2 charging usually provides around 20-ish miles of range per hour of charging.

As for models, there are only three base models (Tesla doesn't go by model years), and the Sports versions of two of them. Lots of colors, however. Each car will have a history, in terms of modifications and updates, and that may be as important as the model choice. Understanding the condition of the battery is the main wear item, along with deciding if you want the 1.5 or 2.x interior layout.

All that said, my Roadster is my daily driver, used for the daily commute to work before retirement, and still taken around town. I've driven it to friends and family over 200 miles away, but that was with some planning since it's still on the original battery. I am very happy to own the car, and consider it an honor to steward it in public.
 
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It looks like a fun car to drive. I would primarily use it for date nights with the wife, picking the kids up from school or extra curricular activities and maybe a few short day trips.

I can see date night or other trips (length dependent on battery). As mentioned, it's 2 seats only .. and while there is a trunk in the back it's not huge if you're thinking soccer balls and such.. ;)
 
It looks like a fun car to drive. I would primarily use it for date nights with the wife, picking the kids up from school or extra curricular activities and maybe a few short day trips.
As a date car, my wife and I would take the Roadster whenever we wanted to go out "in style". Can't be beat for that (possibly with the exception of dealing with valets, which I drew the line at).

As for other activities, perhaps a case study... Years ago we had our second child and my beloved Datsun 240Z was replaced by an Acura Integra GS-R in order to get the two extra seats and trunk space, without giving up too much of the sports car feel. Fast forward a child's lifetime, and in a parallel universe a Roadster's owner was upgrading to a Model S for the same reason. My kids are grown, so the Acura was sold to make way for the Roadster, completing the circle.
 
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The family uses a Model S for the school run and weekends - my 2.5 Roadster is my daily 30 km commuter vehicle - I was previously using a V8 BMW 840 Ci which is 25 yrs old and 16 mpg. The TR's longest trip so far is 60 kms in one day ( Hong Kong )
 
It looks like a fun car to drive. I would primarily use it for date nights with the wife, picking the kids up from school or extra curricular activities and maybe a few short day trips.

Be warned, the car is so fun to drive that even if you buy it as a "weekend" or "date" car, there is a huge risk of it becoming your daily driver. This happened to me, and I'm sure this forum is full of other victims of the Roadster's appeal :)

You're doing your homework, so you're on the right track. As others have said, battery health is one of your main considerations. Tesla offers an upgraded battery for 29k$ that increases your potential range to somewhere around 350 miles. Maximum charging speed is 240V at 70 amps. This gets you about fifty-something miles of charge per hour, but don't expect to charge at this speed anywhere but your own home. Most public L2 chargers are 20-32 amps. So a road trip is do-able as long as it's leisurely and you plan to stop along the way for sightseeing, dining, or what have you. There is a DC Fast Charging (CHAdeMO) retrofit available for the Roadster if you really want to increase your charging speeds (and you expect to have CHAdeMO chargers available).

For day trips, you'll be fine. Range Mode will probably get you 200 to 245 miles (depending on battery health and how fast you drive). If you can plug in at your destination, you should be fine. I live in LA and visit friends in San Diego without issue, even plugging in to 120V while having dinner gets me 5 miles per hour which helps a little.

Speaking of charging away from home, you'll definitely want one or both of Henry Sharp's CAN adapters so that you can charge at a standard J1772 or Tesla Destination charger. There are vanishingly few native Roadster chargers out there (Plugshare lists a dozen in all of California and I know that at least one of those is no longer installed).
 
I strongly prefer the early 1.5 Roadsters (VINs 1-500). Very well built with very high quality parts. These are exclusively 2008 model years, even though some were physically built and delivered in 2009. They are also the cheapest vehicles on the market currently, usually somewhere between $40k and $60k. While Roadsters do lack supercharging, they can be retrofitted to charge on Chademo chargers by @TonyWilliams (CHAdeMo charging for Tesla Roadster). Also, if you get @hcsharp 's CAN adapters (The CAN - Roadster to J1772 or Model S/X connector) then Roadster can use 99.9% of the L2 infrastructure out there.