Like Wayne and others, I've investigated buying a villa many times and put the idea 'to bed' finally when we did actually own an apartment in Germany for a few years. What with the regular bills, needing to rent out and feeling that you
have to visit, it was a relief to sell, despite its having been very useful and paying its way.
Nor would I encourage people to jump into buying DVC even though we have owned for 18 years (and it has worked out
exactly as I had hoped and has been great for us). We bought all of our points from Disney (I doubt there was an active resale market when we first bought) and paid around the mid $60s for most of them - without financing. I doubt I would pay Disney's current prices for any resort, but resale, is a different matter.
I took a long time to make my decision 18 years ago and played with the figures and many 'what if' scenarios, eg, what if air fares become prohibitively expensive, what if exchange rates really dive (it has happened during the 18 years

) because annual dues still have to be paid. One thing I was sure of: I would be happy spending holidays in Florida when the lure of theme parks was a thing of the past - and this has happened. In the autumn I'll be visiting with a friend, when my room rate for a studio at OKW works out at little over £40 per night in dues and in January, DH and I will spend 3 nights at BWV (before a cruise), also for £40 per night

. However, if you want the space of larger villas (as DH and I do at OKW, and again when taking the family) then those holidays 'suck up' points. To us it's worth it, and more importantly, we can afford it.
The key is to do your homework and throw in a few 'what ifs ....' for yourself
