@DBML - to be fair, last year's trip was a bit of a blowout as it was my 40th so we stayed at the Poly which was an absolute dream but it's not our usual. The price also included a few days onsite at Universal. It is an expensive addiction but I don't have any other vices and we are thankfully able to afford it.
I've always wanted to go at Christmas to but it sounds like it's a bit unpleasant which is such a real shame. I'm sorry you didn't have a good time when you went. It's a lot of money to pay to be disappointed. I think late August is a good balance crowd wise but the downside is you're more likely to be caught in a tropical storm or hurricane! Mind you, being onsite during a tropical storm or hurricane is probably as safe as you can get!
@Pomegranatepompom - re: DVC - I assume you know broadly how it works? If not www.themeparktourist.com/features/20170208/32480/dvc-buying-guide-disney-doesnt-want-you-know this is a really good overview (it's little bit old but still fairly accurate). I've been looking into DVC for a few years now and I'm still learning but my overall impression (and this is just my opinion) is that DVC COULD be cost effective IF you go often enough to make it work AND you like to stay in deluxe accommodation (especially in the bigger units like a 1 or 2 bed villa). If you don't mind staying offsite or in the moderate and value resorts then it doesn't make as much sense.
DVC basically allows you to lock in a fixed price for deluxe accommodation at today's prices over the life of the contract , most of which are 20+ years. You exchange your points against stays at any of the legacy DVC resorts (but not any of the new ones like Riviera) at WDW and at their non-theme park properties. You can also sell the contract before it ends and most people seem to make a bit of money when they sell as the value of the points tends to increases over time.
There are arguments for and against buying the points either directly from Disney (you'd get some perks such as money off annual passes and restaurant and merch discounts but you pay a lot more per point) or buying a re-sale contract where you forgo most of the perks but you save substantially on the price per point. For us, I don't think the direct buy perks are worth enough to justify the extra costs so I'm looking primarily at resale. Some people do a mix and match and purchase some of their points re-sale and some from Disney to get around this, so thats also an option.
I am currently looking at a 240 point resale contracts for sale at $99 per point at Saratoga Springs Resort (which we wouldn't mind being our home resort) and doing some fag packet calculations. This works out at $23,760 plus closing costs of $755 - total $24,515 - just under £20k at today's exchange rate for the initial investment. Annual dues would be on top at $6.77 per point so $1,624/£1,314per annum. If we continue to go every other year as we do now, we could bank our points so we had 480 to spend every two years. We'd need around 305 points for a 10 night stay in a 1 bed villa at Saratoga. Currently, to rent a 1 bed at SSR for 10 nights would cost $6k or about £4800 for a stay during the last wek of August. Therefore we only have to do this type of stay 4 times before we break even - in roughly in 8 years for us (without taking annual dues into account). If we only use 305 points every other year, we would have 175 points left over which we can rent out (the going rate seems to be $14-$15 per point), giving us about £1900 back to put towards the annual dues. This means that after 4 trips, we'd potentially be looking at paying next to nothing for our accommodation each trip. Granted dues will increase every year (average seems to be 2-3%) but the time value of money means everything else would increase so it starts to make sense.
I hope this all makes sense but like I said, this is just based on my view and our set of circumstances which may be very different from yours.