Welcome Dan,
Used to own a 99 Miata. Loved it but wanted more car and I got a 2001 Boxster base which I drive year round. Love the car but it being 11 years old I am having to put $$$ into it . I like the way my car is optioned - it has heated seats, air cond. but no remote key entry. Yes, make sure you get the options you want, do lots of reading on the Boxster(rms, ims etc). I would hope the later the model, the less you may have to spend on it as not so much replacement is needed hopefully. Check all receipts on work done . Get a ppi done before committing. Make sure the CEL lite comes on before u start the engine. Be warned you cannot run a Boxster for the same cost as a Miata. This however is the most fun car I have ever owned

. Good luck with search. Trust this helps.