actually, I was suprised at how easily you can work on a boxster(so far). Just look at the DIY threads.
As for which one, 2 months ago I would have said 911 hands down. I was desperately searching for a 911 but the prices were pretty high. I stumbled across a 2001 "s" for a "song" and couldn't say no. So now after driving a boxster for two monthsand if I were in your place, I would probably chose the boxster again. It also depends on the status symbol variable. In my area a porsche is a porsche, meaning a 911 holds no more status symbol than a boxster. actually it doesn't matter to me, as I am over that part of my life.
Unfortunately you may not have the chance to drive both and compare. I think what ever you get you will love. I am a convertible man all the way, so for me it isn't even close!!
Boxster Pros:
1.)
Handling: I love the way the boxster handles. It has a 50/50 weight distribution. Meaning, it goes where it should/you want it to. rear end doesn't become the front end all of a sudden.
2.)
Fun factor: I have had 4 convertibles(this is my 5th), hands down nothing like a ragtop!!!
3.)
Support: Of course I am biased on this, but I have seen more help in the box over the 911 forum.
4.)
Service: I don't know about the 911 but everything I have done on the box has been pretty easy. Belts, plugs, oil, replaced rear bumber, replaced radio. It has been "DIY" stuff and easliy accomplished.
5.)
all season driving: depending on your area(ohio for me), and tire selection, you can easily drive a boxster year round. Wouldn't recommend heavy to moderate snow.
Cons:
1.)
Speed: Not as fast as a 911, but not by much.
2.)
Room: 911 gives you a back seat,but you lose the trunk. I have no family so I am indifferent
3.)
Mystique: For some 911 is the winner hands down.'
4.)
Resale: Boxster's don't hold there value, but if your buying a used one, you are the one benefitting.
5.)
"IMS" Yes I said it.
There are a few things you can do to fix/ alleviate it, but that is another subject for another day.
http://www.lnengineering.com/ims.html