We are in Toronto, so flights to the US are really pricey all the time. It means that we have to plan up to two years in advance and plan to take anywhere from 7-14 day trips each time, so no weekend getaways. That length of time eats up points quickly, even in studios. My mom is coming for two trips this year, so we are getting one-bedrooms for our two winter trips, then a studio for SWW in May. 2 trips a year has been the norm, but we were previously going to all-inclusives in the Caribbean in February every year and for the first time are trying WDW at the same time, so we will see how 3 trips this year goes. Hopefully no burnout, but ask me after next May. Our 6 year-old will have strong opinions, I'm sure

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We bought enough points on each contract that half of each will pay for the MF every year (we rent them out), and we look at where we want to stay for the upcoming UY for each resort so we'll know whether we should rent out, bank, or leave be the points from each resort. There are 3 different UYs so it's not that bad. Hubby made me a spreadsheet so I can plan to my heart's content lol. If the rental market tanks, we made sure that we would have enough annual income to pay the MFs and would have some great vacations, so we've been careful in purchasing. I just didn't want to play the waiting list game for 7-month availability for places like VWL at Christmas, Concierge at AKL, BLT for the Christmas Party, or BWV for walking to DHS during Star Wars Weekends or the RunDisney events, so we diversified.
We bought into so many resorts because we literally bought where we wanted to stay for BLT, BWV, AKL, and now VWL, but OKW is just for cheap points to use to stay at places like Aulani, where we're going for the first time in 2017 if all goes well. We haven't stayed at OKW yet, but I'd like to!