30 years ago we bought OKW during a stay at a Value. We had made trips before and stayed at whatever place looked good on or off property. My first trip was in 1973 when Day's Inn was the rage and my brother and I didn't know the difference. Watching that monorail go around and around and through The Contemporary was mesmerizing!
In that 30 years our son grew from an 8 yo well traveled youngster to a late 30 something married professional. The journey has been interesting, starting with extended family and friends 3BRGV trips to 1 and 2 BR trips with DH, our son and me. Prep school, college and grad school meant empty nester trips for a decade, but we typically went during F & W and had a great time. I think DH and I have only stayed in a studio a few times and he is adamant about having a WD and so am I as it makes the trip so much easier. We don't cook much but stock lots of drinks, fruit, salads and always a frozen pizza for that rainy night.
We are off and on AP holders (on right now) as we try to use it over two longer trips in a year (10-14 days each) so it makes sense. Perks are helpful when our foodie kids are with us.
Until recently we almost always had a rental car, but this next trip in May will be 9 nights at BWV in a 1BR so there is no need for a car. We will be at EPCOT most of the time and will bus to other parks if we need to. We plan to take the Minnie Van to/from the airport as we are saving a ton on the rental car. Now that SWA announced it will deliver luggage from your home airport to your WDW resort I am thrilled! That was the biggest convenience and losing that perk was a PIA for DH as I use a WC at MCO. If there isn't an attendant (often) and sometimes not even a WC, rolling 2 bags and dealing with me is a challenge.
We always invite our son and DIL as they live 3000 miles from us now and have given them many solo trips as well. We love it when they go and we give them a studio at the same or different resort. Lately they have been going to Europe and will be there in March so we won't see them in May. We're planning October and our son may have a medical conference in Orlando so we're hoping they can join us.
We've gone from 230 points in 1996 to 650 or so post covid to 225 now with direct and resale. I often use the OTU points option and can get 48 between direct and resale. Better than buying a bunch of points. I've transferred in points but now that is not so easy as it is one time per year. I'll be smarter about transferring in a larger amount if necessary in the future for bigger trips. Disney is expensive and we are more about getting what we want and save by not eating out much at home the rest of the year, using SWA points for flights, using cash back credit cards and buying discounted Disney gift cards when possible (even to pay for dues). It all counts.
I hope you pick up a tip or two and enjoy your trips!