If I had all of the cash to drop I would be all in, financing is a non starter for me. So maybe I continue to save and re-evaluate in a few years? The only catch is I have a hard time stomaching spending the cash if we were to go at any time in the next few years knowing I could be saving in the long run. Does that all make sense, haha?
Keep in mind that we are a bunch of enablers, and we will talk you into 300 points direct if you let us. It is reasonable to buy what you can without financing. And while dues might eventually be a big part of your total costs, that doesn't help you with your cash flow today. So in addition to looking for the right Poly resale contract, I think there are a few other ways to go about this.
First, you could consider a different resort resale. While the Poly is a lovely resort, it may not be the only resort you find that you love. What's more, it is not
that hard to book Poly longhouses with non-Poly points, becasue there are a lot of them. That
might change as the Tower sales continue, becuase that changes the mix of owners, and that owner mix may dis-proportionately prefer the lounghouses. That doesn't seem to be happening yet, but that could be just because the tower has that New Resort Smell.
But, if there is another resort (at WDW and in the Original 14 set, but probably exclusing the 2042s given what I assume are your ages) that you think you would enjoy, the cost to own a smaller contract at one of them might not be so prohibitve and/or you could afford more poitns to start, so you don't have to put off trips as long. The set to look at for this are, in order of expiration: SSR, AKV, BLT, and CCV. That might be the resort you stay at more often than not, but you'd still probably be able to check out several others over the course of a year. This will give you a sense for what average costs will be for each resort, and at each "band" of contract sizes. Of course, this is just a ballpark guide.
https://www.fidelityrealestate.com/blog/july-2025-average-dvc-resale-price-per-point/
Second, you could start building a portfolio of direct points by being strategic about when you do it. You can buy as little as 25 at a time, and you can buy two direct points at Poly for about the cost of every three resale. Again, based on what I assume are your ages, I suspect you will find more value than most in owning direct points, becuase over time, more resorts will be restricted---not only the new resorts Disney builds, but presumably also if and when they recycle expiring resorts.
Here's what I mean by strategic: suppose I wanted to travel sometime in April next year, and visit in the springtime most years. Right now, April is still in the Home Resort booking period. If you normally imagine traveling in the spring-ish time, then good UYs include December, February, and (maybe) March. Let's use February. You can buy 50 direct points today which sounds as though it is in your budget, and your first year (UY25) would include dates 2/1/25-1/31/26. You can bank those points to UY26, and borrow from UY27, for 150 points---enough for a decent trip. Then, in 2027, you can do this again with maybe 25 more points that you've saved to buy between now and then, banking 2027 into 2028. But what's cool about this is that you will get 75 points coming in UY2028, so even though you are only banking forward 25, that still gives you 100 before you have to borrow anything. You might have to be aggressive about saving to have enough for those 25, but maye that is within reach.
The third option is to keep going on trips now, but do them "on the cheap." Remember that DVC only really saves you on lodging. You still have to buy theme park tickets, and food, and you have to get there, all of which costs money. But, DVC is not the only way to save on lodging! You can "rough it" in the Values for a few years and plow the savings vs. "what you would have spent" into your DVC fund. While you are at it, skip the "extras"---don't do more than a handful of sit-down meals, skip hopping, and don't buy Lighting Lane, and put every single dollar "you would have spent" into your DVC fund. See a cute $80 sweatshirt you want? Congratulations! You just added $80 to your DVC fund.
(Talk about enabling.)
You could even (gasp!) stay offsite. I know this is blasphemous, but hear me out. There are a LOT of places to stay just outside the borders of WDW, and some of them are both pretty nice and very inexpensive. This is what we did when we started out, and while an offsite stay is different than on onside one, the two vacations are much more alike than they are different.
