I had been working on other cars (my own) for many years before I got a Boxster and had the same concern. I have actually found it quite easy to work on compared to many other cars. Just put together a little differently. The brakes are actually the easiest I have worked on, but I did pick up a new tool when I flushed the brake fluid.
In fact, the Boxsters have been a good excuse to buy new tools as I proceed with more maintenance.
I have bought three 99s. Sold one and plan to keep two. A good year IMHO.
Rather than rambling on, I'll just tell you to browse topics and read the Forum. All the info you need has been posted already. Ask if you have trouble finding.
Edit: Oil changes can cost that much, but generally it's just a matter of buying about 9 quarts of
your choice* full synthetic oil, a filter, and crush washer. For me, a bit over $60.
*Do not ask, "what is the best oil". It's like standing in a crowd outside a Trump Rally and asking who to vote for. You'll get opinions, but chances are someone will walk away bloody. Search and decide.
Good luck and welcome to the forum.