Thanks to everyone that contributed with opinions and help! It definitely helped me figure out a lot of our travel plans. I'll be leaving in less than 2 months, and am SUPER excited!
We have decided to drive Milford Sound ourselves...I will have a Kiwi behind the wheel, and she's comfortable doing the drive. Just hope the road doesn't close (funny, some say super high risk of closures in winter while others say it's not too likely).
We will drive from Qtown-Mt Cook and spend 2 days on Mt Cook. Was hoping to do the ARGO tour, but they're taking the month of July off for maintenance. So we'll spend a lot of time just walking and exploring during the day, and hope to get some great star gazing done at night. I recently saw some photos circulating of the Milky Way from Mt Cook and it's absolutely stunning! BTW, it turns out my Kiwi friend's great-great grandfather was one of the men who first climbed Mt Cook back in the day!!!
From Mt Cook I think we will head the Chch and spend a night there to break up the trip. Then head through Arthur's Pass to the west coast, and overnight in Punakaiki. The rest is still a bit up in the air, but at this point we are fairly close to Blenheim where my friend lives, and so basically close enough to home to sort of wing it.
I'd like to go through Buller's Gorge, as it sounds and looks fantastic. Def want to hit at least one winery tour, that is VERY important to me as I am a wine lover, particularly Marlborough SB's

Still trying to figure out a way to fit in Hanmer & Kaikoura into the end of the trip.
I am ever so grateful for everyone's input and comments! My only disappointment is that because I'll be there in winter I won't have the chance to do some really cool things. Guess I'll have to come back!