I've had my Boxster for a year and 5000 miles so thought I would do a quick take on my experiences so far, it being my first foray into Porsche ownership. Mine is a 2009 987 gen 2 with the 2.9 flat 6 and PDK gearbox. When looking for a Boxster I specifically went after a gen 2 car as I couldn't stomach the potential engine problems of the gen 1 cars. PDK was also a must for me and as this was only introduced with the gen 2 cars, a gen 1 was never really on the cards.
Performance wise it was always going to be slower than the E46 M3 I had previously, an equivalent 3.4 S was a good £5k more at the time which was more than I could afford, but truthfully, after a year the performance is enough. 255BHP is not loads but the ratios are short, the gearbox is fast and clever at reading your throttle inputs and in a point a squirt way, 0-100mph ~12seconds, it's quick enough. The engine is a gem, it sounds great but could be a little more raucous, it spins so smoothly and has a great howl up the range.
To focus on performance would be missing the point though. People seem to knob on endlessly about the steering in this era of Porsche but they do have a point, it's brilliant. Great weighting, very communicative and very accurate, if and when I move on to something else it will be an area I miss a lot. The handling is very neutral and balanced as you would expect, there is a lot grip but not in an inert way. Mine has the regular passive dampers rather than PASM and the ride is never harsh, it doesn't smash over bumps like an S Line Audi, and it only gets better as the speeds increase. It's really good fun to zing down a country road which is the whole point. I do miss the fun of the locking diff from the M3 so I would look to option one given the choice but it's not really a lairy car in that way. There is never any sense that it's going to snap and catch you out like my S2000 would do.
What's surprised me? It's very comfortable on long journeys, much less road noise than my M3 and you don't have to raise your voice to have a civilised conversation on the motorway like my S2000. It's very practical, as long as you don't have to transport anything too long (and even then you can take the roof down), it can swallow a lot of luggage. It's economical, it'll do 36mpg on a run and 450 miles on a tank so it's great for covering distance. It suits my usage (mostly weekends away) really well.
Running costs have been mixed. On one hand it has been faultless minus the original battery dying in a cold snap in Scotland. On the other hand it just had a major service done at Porsche (I didn't want to break the dealer service history), which was over £800 which is a bit mental given there's nothing that exotic about it. However, that's every two years and included plugs so would be £500 for a normal one every two years which is not too heinous.
What would I change? It would be nice to have the later sports PDK wheel with paddles rather than buttons but it's not worth £1k to me. Aesthetically it sits quite high but I fear I'd just bugger up the ride if I lowered it so that'll stay as is. Otherwise a proper diff and sports exhaust would give it a bit more attitude but as I'm not sure how long I'll keep it so I doubt I'll mess with it. Although given that prices of anything vaguely interesting are now mental, I can't see this going anywhere for the time being.
Tl;dr summary, brilliant thing, would recommend.