Speaking as 38 year old contractor with a PhD and about to start my CPL and ME/IR guess which option I'd recommend?
Not sure which university you're thinking of doing the PhD at, but in my experience it opens doors and is very useful when it comes to a back up career/one that pays for flying. In my experience having a PhD makes interviews (only non-aviation so far) a breeze, so your back up career should be fairly straightforward.
No doubt the PhD will count for a lot less when it comes to securing that first flying job but it's a help with the back-up/regular work.
Perhaps I'm too old to seriously try this flying for a living lark but I'm going to give it a damned good go. You're only approaching middle age once and I reckon I've got at least 3 or 4 mid-life crises to enjoy! You're a mere youngster, get stuck in!
Go for option 2 and if the girl's got any sense she'll stick with you.
...and if she doesn't, can I have her phone number?