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Back to the OP's question, 914 or Boxster.
I have had a few 914s and found them to be fun and in the past extremely easy to work on by myself. But, being that they are all getting to be around 40 years old they are definitely archaic, as am I. I have found that my body no longer bends into the proper positions to work on a 914. So, another 914 is not on the radar for me. And, good luck finding a shop that knows the 914.
My next Porsche will either be a Boxster or a 996. Modern conveniences and comfort. I doubt that I will be able to do too much work myself when I pick one of these up. But, I can find quite a few shops around here that are familiar with the Boxster or 996. Oh, and since my track days are over, the next one will be a rag top.
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