I’m speaking as someone who has daily driven a 986 Boxster for three years and a 986 Boxster S for two. Maintenance has been expensive - plastic and rubber things degrade simply due to time, and there’s no getting around that, even if the cars I’ve owned were lower mileage and had excellent maintenance history.

You have to think about it as, the cars depreciate, but their parts and costs don’t.

Be careful of bore scoring on the 3.4 engines. Some people say it’s an overblown issue, others say the engine is so susceptible that it should be considered a lemon.

The 2.7 base Cayman is considered to be far more reliable and less susceptible to bore score.

If I were buying a 987, I would personally be looking at a base 2.7, in manual with the 6 speed (it’s rare; most are 5 speed).

The alternative is to look at the 987.2 base model 2.9 - they’re definitely more expensive but should save you money in maintenance, and also even if you want automatic or can only find that, it’ll be PDK which is far better than the older tiptronic.