I think you have put a lot of though into this purchase, but the one thing I can not get past and feel it is worth bringing attention to is your frequency of your travels. If you are truly only planning on going every 3-4 years then
DVC often is not the safest choice. The reason is if you have to bank, use current points and borrow to put a trip together then you run a very high risk of losing points if you needed to cancel.
Maybe I wasn't clear. Our plan is to take 3 trips in every 4 years span. Basically giving us one free year to do something other than Disney.
You already mentioned that SO is a teacher so your travel times are very limited. Lets say you do buy that March UY and you plan a trip for end of August, so July rolls around and you have to cancel the trip -- you would then have to first off cancel 31 days prior or the points would go in holding, then if you did that you would have to book a trip prior to Feb 28th of the following year to avoid losing those banked and borrowed points. It isn't impossible but you would be pretty limited from September to early January due to it being a very busy DVC time coupled with your SO school schedule - so if you couldn't reschedule then only your current year points could be banked for further use.
With the help of this thread, I'm thinking a February use year would be the best choice (please critique) for the following reasons.
1. If we have to cancel our July/Aug trip more than 30 days out, we are still in the banking window for a few months, which gives us time to reanalyze.
2. If we have to cancel our July/Aug trip less than 30 days out (hopefully this would only be in extreme circumstances), there is still 5-6 months to rent out the points before they expire. You are right, we likely wouldn't be able to cobble a way to use them in that time frame.
3. While 90% of our vacations will be in the summer, there is a potential that once in a while we may do a March Break vacation. Having a use year before April makes this possible.
4. There seems to be much more Feb use years out there at Saratoga than March. This will make it easy to find resale points with the same use year down the line.
maybe just looking at one SSR contract resale would make more sense vs direct SSR and Vero - Vero is very easy to book at 7 months and the MF are very high compared to SSR.
On a direct 75 point SSR contract, ignoring the assumed spread between US inflation and maintenance fees inflation, the break even on the maintenance fees is about 16 years. With only 23 years remaining on the contract, the difference is only about $525 USD on a 25 point contract over 23 years. The cheaper upfront cost (especially with the current USD/CAD exchange rate, there may end up being zero long term difference), is worth it.
On a resale 75 point SSR contract @ 120 PP (hopefully with full 2019 points), the upfront cost difference is about $2,500, but there would be a ~$75/yr difference in maintenance fees (25 points at Vero vs SSR). In the second year alone, we will save about $1,100 on ticket costs using the membership perks.
One of my biggest reasons for going direct is the ability to use those points to book at Riviera, Reflections, and any other new resorts over 23-35 years of ownership. It's easy to say now that it's not a big deal with only one resort that hasn't even opened yet, but in 15 years, there may be 6 to 7 new resorts in different parts of the world. I would hate to not have the flexibility to try that, even if it's for a nominal premium.
Even more importantly in 2042, 3 of the 10 legacy WDW resorts may disappear. If current restrictions stay the same or even tighten up, your going to have a whole bunch of resale owners from the 9 remaining legacy resorts plus all of the new resort direct members trying to transfer at 7 months. The only difference is you will not be able to transfer to any of the new resorts, while they can transfer to all. This may make it nearly impossible to book anything but your home resort. It's hard to really know what will happen at that point, but I'd like to keep some flexibility.
Thanks for the input!