It's sort of funny that I noticed this topic today, since this morning my six year old was looking at pictures from our trip when he was 3 and telling us what he remembered about that trip.
We took our DS the first time when he was 2.5. He had a great time, but he doesn't remember anything from that trip at all. We stayed at the Boardwalk, because we like Epcot best and we like to walk there for dinner. (We also like to be able to walk to DHS, although its our least favorite park.) That first trip was a week long, which is really longer than DS needed. He was scared of the characters, would not go on any ride that looked at all frightening to him (which included Dumbo), but he loved the pool and went swimming every day. He had a very good time, and it was a fun trip, but quite honestly, it was for us as much or more than for him at that age.
We made the next trip about 9 months later, and stayed at the Grand Floridian. We knew we wanted to stay at a monorail hotel for Magic Kingdom access that trip, and the GF appealed to us most. This was a shorter trip to WDW, just 4 days, because we also spent 4 days at a resort on the Alabama coast. Our son loved this trip, and still remembers it and talks about it. He still didn't love the characters or a lot of the rides that seemed scary to him, but we had a good sense of what he would and wouldn't enjoy at this point, and didn't push him to try things we knew would stress him.
The second trip (when he was just shy of 3.5) was good enough that we knew we were going to be visiting WDW pretty much every year, sometimes twice a year, and so we finally bought DVC. We'd been considering it for a while, since DH and I both enjoy WDW, but we'd switched to doing cruises when DS was really little because cruises just seemed like easier and more relaxing vacations with a baby.
I agree with the people who say that if you're only likely to make one trip in the next few years, you might want to wait a year. 3.5 is a good age for a trip to WDW, but a child is likely to get more out of it a little older. If you think you might do one trip now and another in two or three years, I'd say go ahead and do it.
As far as the money goes, $6000 is a lot of money. Don't get me wrong, we always stayed at deluxe resorts club level before we bought DVC, but we always got some sort of deal that made the prices a little less insane. (We got a "buy x nights, get y nights free" deal one year, free dining a couple of years, and straight discount codes sometimes.) We didn't go when we couldn't find some sort of discount, but we were flexible about when we traveled, and eventually always found a discount. (I know there are people who love the values and moderates, but quite honestly, for us since we could afford it, it's been all about location, location, location, particularly with young children.) When we actually purchased DVC, we did it because we were pricing another many thousand dollars vacation and realized we could buy DVC for not much more.
The only people who can decide if the expense is worth it are you and DH. You will have a good time if you go, but you can also have a good time if you find a less expensive vacation. (Our DS loves to cruise, as it turns out, and we can often cruise for a lot less money than it takes to go to WDW.)
Good luck with your decision!
Best wishes!
All he did was get pushed around by my dh while me and the girls went on all the rides. That was just the kind of kid he was...very shy, very nervous. All he remembers from the trip is eating pretzels in the stroller! On the other hand, we went when my oldest was 2 1/2 and she had a blast. All she wanted to do was meet the characters and go on a ride once in a while.
