How much more for an S?
 

Just curious, how much more should an S cost over a base model of the same year. All things being fairly equal? For example, in Toronto a 2000 base is about $11,000. I have seen S models same year for about $1500, to $2000 more.
Is that about right? And is the S worth the difference in price?

That sounds about right. If not a bit on the cheap end, the S is worth it, as it was 10k more new. It's more than just a bigger engine. However It would be harder for me to decide between an S and a 2.5, the 2.5s can be had very cheap, and are very lightweight.

I bought my car used about 8 years ago, so I'm not really familiar with pricing anymore. That said, a $1500-2000 premium for an S seems like a good deal to me.

However, I wonder if the price comparison is for cars with similar mileage and in similar condition. If the 2000 base has 60,000 miles, all service records and looks like someone loved it, it may be a better deal than a 2000 S with 120,000 miles that someone neglected.

My S
 

When shopping for a good well kept Boxster 15 months ago I noticed all low milage S models were 2 to 4 thousand more than a standard. Given the improved suspension, Brembo Brakes and increased HP I think it is a deal. I paid 15K for my 2001 with 65K on the clock.

2 to 4k more with everything being equal. Worth every penny in my opinion.

When I was shopping 8 years ago, the difference seemed to be about $10k. So the current differential seems very small. Also, S's seemed to be more highly optioned so they are more likely to have niceties such as heated seats.

How much more for S?
 

To answer if it's really worth it to get the "S" I'd say Yes! But the bottom line here is the condition,options, and history! Good luck with your search..

I got my 2001 S for 14.5k with 55k miles. You can never have too much power in a Boxster and many folks spend thousands on performance mods of all sorts to get a few HP here and there so buying an S for $1k-2K more is worth it, bigger brakes, more HP, thicker cylinders (Room to bore out the diameter and get even more power if you just can get enough) and a bigger smile.

Also if you pick your serial numbered car carefully you can have double row IMS bearings which are also more robust and less prone to IMS issues, 1% failure rate vs 5%+ failure rate for the single row IMS bearings.