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Jack ..
I'm 71 (btw .. gave up motorcycles in my early 30's for something safer - flying) and just went thru the process choosing a boxster.
Not sure my experience is one to follow but I'll outline it (I'm certain there are many more who will add valuable information/onsight) .. (note the opinions below are my own and personal) ..
1 - set an initial budget to include both car purchase (and assorted fees) plus repairs needed up front .. I found a basic correlation for any specific model - lower the price higher the initial maintenance/repair cost
2 - familiarize yourself with generations ..
a - '97 - '99 - all dual row IMS shaft bearing with less probability of failure/all 2.5 l engine /snappy responsive fun but not overwhelming power (I'd steer clear of '97 as no side airbags)
b - 00-04/5 - IMS bearing problem to be aware of /more options available/ 2.7 l base and 3.2 l S (some carryover in 2000 of 2.5 l)/good refinements and more powerful while losing tinge of driveability
c - '05/6 - '08 - to me, rather like the original Mustang growing abit more comfortable but at the expense of that 'feeling'/ radical change in IMS inside block late
d - '09 - '12 - a definite change towards a touring car with comfort options/ IMS problem designed out/ PDK transmission/ 2.9 l base and 3.4 l S
I would definitely get a listing of factory option available by year and changes (many available on internet) and test drive extensively starting with '98- '99 2.5l to see what 'feel' captures you .. each group and engine option while checking the available options that can enhance you ride (ie. stability control, sport suspension, power/heated seats/litronic head lights etc) - AND I would make my test drives at a dealership - even potentially at a specialty dealer who has several different boxsters in inventory.
3 - approx year and options decided (remembering it's usually better/cheaper to get the options you want ON the car and not retrofit) .. shop for it. I used Craigslist, cars.com, cargurus, autotrader as well as pca website. By the time I was ACTIVELY shopping I knew what I wanted .. specifically (including color/s)
4 - PrePurchaseInspection I believe is mandatory as the sins of the past are sometimes well hidden (at ~$300 can get expensive if you don't prequalify well)
a few other points ..
only ~you~ know how much you will wrench on it .. be realistic when determining repairs/maintenance ..
btw - I thought I'd never by from a dealership but .. I found just the boxster that checked all my buttons .. paid perhaps abit more than I should have but .. .. it is in excellent condition
Good luck .. enjoy the ride .. it's a fun process that took me 6 months to complete and well worth every hour I spent ..
~and~ don't be afraid to ask questions here .. the knowledge and experience found is outstanding
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