I would not be too dismayed at the relatively small problems you have been having (ebrake, gas cap, rear window), these are really pretty small when you put things into perspective....I was fanatical to a degree about the condition of my 98, seeing every chip, swirl mark, etc....Its a 7-8 year old car for chrise sake! Normal wear and tear is to be expected is what I am saying.....
On the subject of having the car serviced, that is just terrible, you deserve better service, so if I were you, I would find an independent mechanic who you trust and is experienced with the Boxster.....Now that you do not have the warranty you no longer have to probably go thru a dealership mechanic...There are other good ones out there, you just have to find them!
If regular maintenance and the possibility for bigger repairs down the road scare you, then maybe its not for you.....Hell, I might be with you once my warranty expires in 2 1/2 years!

...Hopefully not tho, I love driving this car...
Lou