Porsche Reliability is in the top ten of auto manufacturers. Boxsters have been above average in most categories, but average to below average in engine problems across all model years. So far Porsche has been frequently generous about fixing engine problems including many fixes outside warrantee.
97-98 warrantees expired in 99-00. 99-04 Boxster come with 4 year warrantees. There is no good way to predict/check for a Boxster engine failure. I feel like a bit like a prophet of doom - but I mention the engine because you asked.
Another weak area has been the convertible top. As far as convertibles go, the top seems to be above average, but it seems all convertibles have top issues. In 97-98 there is a top transmission problem which is a DIY fix, not to expensive and well discussed at RENNTECH.ORG. The other problem with the convertible top is that folks sometimes try to operate the top below 35 degrees and the plastic window cracks. Repairing this can be VERY expensive. If you really like top down driving in 30 degree weather(like me), you can rig up an electric blanket as a window warmer. The more common solution is to keep the top up when the temperatures approach freezing.
Engine access is not bad.
Half raise the folding top - unsnap 4 places, undo 4 hand tight twisty thingies, remove carpeting and an optional storage box, and untwist 5 more hand fasteners and the top of the engine (airbox, intake, etc) is exposed. 3-5 minutes-no tools.
OR
Tilt the seats forward. remove 5 decorative nuts by hand, remove carpeting and about 6 more bolts and the front of the engine(pulleys, belts, etc) is exposed. 3-5 minutes - one wrench.
Admittedly, 3-5 minutes is more than 20 seconds to pop a hood, but in engine repair terms this isn't a big deal. For checking water and oil, one merely looks in the trunk, which is equally convenient as looking under a hood.
All Boxsters have spoilers that retract, unless someone has done an aftermarket thing to put on a fixed spoiler. 97-02 spoilers are straight, 03-04 spoilers have a curved surface when closed and viewed from above. There is a switch left of the drivers left foot to raise and lower the spoiler manually if you want to look at it while standing still, otherwise the spoiler goes up at around 65 and back down at around 55 mph.
97-98 Boxsters have 2.5L engines, 99-04 come with a choice of 2.7L or 3.2L(S) engines. I prefer the 250/258HP 3.2L
I consider a seat heater a great option in any year Boxster! I used my seat heater in Arizona winters as well as NY winters.
Hope I didn't scare you with the reliability answers. Porsches are a lot closer to BMW reliability than Ferrari reliability.
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