Thank you everyone for your words of congratulations!
Now that my fiance and I have agreed on the wedding we want, I don't see myself coming ahead at all this year - our wedding is going to cost a little more than we thought it would...
Here's the breakdown of things:
I have 3 credit cards: one of them has a balance of $0, one of them has a credit (I had booked an expensive tour for our last WDW trip, had the credit card paid off and then cancelled the tour) - so I've been trying to charge things to that card to bring it back to a zero balance (and since I've previously paid off the tour, it's like found money!), credit card #3 has a balance of about $2500 owing.
I also have 2 lines of credit, with a balance owing of a little over $18,000.
I have a decent emergency fund of about $6000. We will probably dip into this a little for wedding costs, but I have insisted it remains above $5000 at all times. I have also saved a decent amount to cover our DVC rental for our trip next January, but it's still not enough to cover it completely (especially when you factor in the terrible exchange rate).
We did the math, and it actually makes sense for me to buy a Premier Pass for Disney - the one that is valid in both Florida and California. It's crazy expensive, but with a trip to DLR next week, another one in November and then our WDW trip in early January, we'll come out ahead in the long run. Unfortunately I now have a $1500USD charge to put on my credit card next week (which is about $2000CAD). We are only buying one, since it is cheaper to just buy tickets for my fiance, but the annual pass will work out because of the Photopass pictures and food/merch discounts.
I think this is the year we try to create good habits when it comes to our money, but just accept the fact that we will be a little farther behind by the end of the year. But hopefully with good habits in place, we can crush 2018!
Luckily, my fiance and I don't buy each other presents for Christmas, birthdays, anniversarys, etc. We always take a trip in January, so we don't need the added costs of Christmas. Both of us have birthdays in January as well, so we call our vacations our birthday trips (my birthday was a day after returning from WDW, so we went for lunch at Olive Garden but kept it cheap). We actually fly to California on Luke's birthday, so I told him that's his birthday celebration haha. We do the same thing every year for our anniversary - go for supper at the hipster pub we had our first date at (the food is amazing!) and then go to Stars on Ice (yes, figure skating. It's always here the week of our anniversary, so it just works - plus both of us enjoy watching pretty much any sport). We're going to get our family on board with no presents for Christmas next year, since we are planning a destination wedding and everyone will be paying enough just to come with us.