As someone who just went through this, here are the starting points IMO, all of these have several youtube video explanations for. It helps to watch the same thing from multiple sources so you get different perspectives.
1) Direct vs Resale: based on cost, with resale being around 50% cheaper, I knew right away that I wanted resale. But other people value the benefits of Direct, so research what those benefits are and what you'll be losing out on by buying resale.
2) Home resort: All resorts have there pros and cons. You need to understand what you value in a resort, what kind of room you'll most likely stay in, and whether that resort is easy to book at the 7mo mark. I was really leaning towards AKV first, but then realized it was relatively easy to get at 7mo, so I went with a different resort that I was happy staying in.
3) Number of points: Addonitis is real and happens even during the buying phase. We were first looking at contracts from 100-150 points and somehow ended up with 350 points. Again look at the type of room you'll most likely stay in, how long you'll stay for, and what time of year. For us we started considering a studio but realized we would be more comfortable in a 2br, so that's what we purchased for.
I think the above is a good starting point. Once you've got a handle on that you can start reading more into the fine print and intricacies.
Just to further expand on the points you already made
1. Direct vs. resale.
Direct Pros:
- Able to book any and all resorts
- Ability to buy Sorcerer pass at Disney World which otherwise is only available to Florida residents
- Access to Moonlight Magic
- Access to DVC Lounges which are not available to resale members at
Disneyland, Epcot and at Bay Lake Tower
- 20% discount on merch, 10% discount on food
- points instantly available and loaded into your account
Direct Cons:
- Significantly more expensive buy in cost compared to resale (can save 10s of thousands by buying resale) so do not discount this con
- typically can expect to lose more money if needing to sell the contract in the future compared to buying resale
Resale pros:
- Cheaper buy in cost
- able to recuperate cost without significant loss generally speaking if needing/planning to sell
- Able to pick use year (the importance of this takes a little bit of time to wrap your head around so I won't try to explain it in this comment)
Resale cons:
- Unable to book Riviera, Villas at Disneyland Hotel or Cabins at Fort Wilderness and every other new resort that is not added to an already existing association (unless you buy resale at RIV, VDH or CFW in which case you can ONLY use it at their respective home resort)
- pretty much you don't get access to the stuff I listed in the direct pros
- still paying the same amount in dues which make up more than 2/3 of the price of a contract over it's lifetime
I'd say a lot of us own a mixture of both resale and direct points AKA have hybrid memberships. This allows us to enjoy the full benefits of membership, but also get a significant discount on a lot of our points. IMO though, the only real tangible benefit of buying direct is being able to book any future resorts as all the other benefits are subject to discontinuation at any time. Also the things like merchandise and food discounts are available to you if you have an annual pass so if you're planning to buy a pass or already own a pass, this makes this perk less important.