My Boxster S has been my only car for over 11 years and I drive it year-round, although it is not a daily driver. I mostly ride one of my six bicycles :o.
I'm a little skeptical on the idea of storing the car for winter. Even if you store it correctly by immediately changing the oil before its rolled into storage (so that the oil 100% clean as possible) engine components dry out/get brittle over time. One of our resident engine experts recently described engine oil as lifeblood, and blood usually works best when its flowing and not stagnant.
We have a forum member here FloridaBill who has 300K miles on his daily-driven 986 and has had no major engine issues, and wasn't even aware of the IMS issue. Although reading his posts he followed a very strict maintenance regime. My take away from that is that a car that never sits for too long, and is driven at least an hour or so to burn off all the engine build up say once every week or two, running a high quality oil (I use Motul now, previously Castrol Edge and Mobil 1 initially) is better than an engine that spends months in storage each year. So your questions are spot on. But at the same time you want to avoid all the daily ice cold engine starts, we had some real doozies this year with below 0 zero temps. I cringed when I fired it up those few times, I should have just called an Uber even if it was far. And the other issue is that there's just more crap on the roads during winter that kicks up onto the paint, more pot-holes to tax all the suspension, mounts, etc. -- more new and annoying rattles. Having a second car really solves this completely.

p.s.
I just picked up my car from having the bumper repainted yet again. The shop has a PDR (paint-less dent repair) guy that is top notch. He was charging $75 per ding, which takes him all of two minutes to pop out. One penny-sized ding on each corner and he's done for the day. That is a great business to be in.

I split my driving between a bright yellow Mercury Milan (manual!) and my Harley so my plan is to drive the Boxster 2-3 a week spring through fall. During the winter I plan to drive it for an hour or so every week or two when the roads are clear and the temperature is reasonable (20ish+). I do the same thing with my motorcycle (yes, even in the winter).

I haven't decided if I want to try to rack up hundreds of thousands of miles, a la Boxster Bill in FL, or keep the miles down and sell it in 4-5 years. A large part of me wants to see 200K on the odometer years down the road but time will tell I suppose.