I don't disagree with OP regarding buying a smallish resale, however you do pay a premium. When you decide which DVC you are interested in look at the price for contracts in the 100+ range on all the resale sites you can find. That "average" price should give you more of a target price along with the ROFR thread here on disboards. I continue to buy 100 or less contracts, but I target lingering contracts I can better negotiate on. I've also been doing this for 25 years, so I can do the math quickly. Digging in and doing your homework will pay off for you as you want to get that offer in quickly and move on if you don't get it. I will pay a bit of a premium for a small contract but not $20 or $30 more PP. I always buy knowing my contract is worth more in a flip than I paid for it (and I have profitably flipped many contracts over the years).
Your UY can be an issue depending on when you go. This year, lots of people with expiring spring points were caught off-guard and this could have happened to any of our UY's. We almost always go to WDW for Halloween so we have an Oct UY. We bought two more contracts at a different resort recently with a June UY. Though not ideal, we couldn't find anything for Oct and it will work for us as we are still in the 8 month banking window. UY's that have many available contracts will likely be more competitive - supply and demand. Do some thinking about UY before you jump and understand banking and borrowing (50% currently). IMO loaded contracts with banked 2019 points have a value if you have time to rent or use them before they expire. I buy loaded and rent, however the rental market isn't as good as it was for obvious reasons. One of my new contracts has 2019 points (seller paid MF's) I will rent and that will bring my PP price down accordingly since it is all profit except the taxes I pay on the income. This has been my MO over the years and reduced my out of pocket dramatically.
Direct vs resale. 100 point minimum is going to 125 at the end of September from the info I got directly from my DVC Guide on Monday. It is still considered a rumor here, but I have no reason to think he isn't telling the truth. Most people here will agree that buying your ideal resale contract
first and then matching up direct after is easier as you are able to choose from the broad selection available and go after price. Unfortunately, the anticipated deadline throws a curveball for those going in that direction. AP's are not available right now, however my guide suggests they won't be going away permanently. That would IMO kill direct and I hope DVC clarifies this soon.
After a dip this spring the
asking prices seem to be rising steadily but I'm also seeing lots of contracts lingering and being reduced (those are my targets). I just read today that the ROFR train has started again (thread on disboards) but I wouldn't let that hold you back from making a lower offer. Six contracts taken doesn't make or break the market IMO. If you want a 2021 trip, get moving now. You want the 11 month advantage.
To finish this lengthy answer, buy the resort you love and buy enough points to satisfy your needs even if you have to buy multiple contracts over the years. Spend some time at the kitchen table negotiating with each other and write down your dream contract and let the universe help you find it!