Disney

"I'm sure people would say their 2 year old enjoyed it, but as you point out--it's quite expensive. I grew up growing to Disney (lived in FLA) and worked there a semester of college.

However, if you really do want to go, in answer to your questions:
1. I am a HUGE proponent of staying 'on property'--it gives you the full experience, is so much easier, and there are some benies that staying on property get you, such as entrance to certain parks an hour early on certain days--only avail. To those who stay on property. With a small child, I like this option. Also, you will not want to spend all day, but may want to go in the morning, and again in the late afternoon--and if you parked there is the hassle there, versus just hopping on Disney transport.

That said, if you use a bus to get to your Disney hotel (which you will if you stay at a value resort), do try and avoid the worst of the rush hours, as the buses get crowded--Disney tires to add extra buses an be efficient, but just keep in mind.

2. As mentioned, parking IMO is moderately inconvenient but more so is getting lost on property. Like DC, which was laid out to get attacking forces lost en route, Disney was laid out to appear bigger than it is, with lots of loops and making you take longer to get from A to B than would appear necessary. I come from the school of park your car and be done with it.

3. Haven't driven to FLA in years, can't comment on quirky stops.

4. Not sure about any reduction in crowds on xmas day--if anything, I suspect people there to vacation are there to play, there are books out now that will tell you the least crowded days of the week, I guess I'd aim for those, but truly, there is a reason you are playing peak rate at the hotels.

5. Park hopper--yes yes yes. Esp. if you want to maybe visit one park in the morning and another in the afternoon--again the books give info on parks that tend to be more crowded in the morning and less so in the afternoon. Plus, they don't expire, so as long as your kid fits the age requirements--and if you're thinking of taking him at 2.5, I'm guessing you'll go when he's older too. We just tuck away any unused day tickets and have been able to use again years later.

6. I don't think there is a big difference between 2 or 3 days. Maybe if you are worried about cost, you could initially stay somewhere that is just an hour or so from Disney (esp. since you are driving), go do Disney, check into a Disney resort for 2 nights, and then in the afternoon on the 3rd day, drive a short distance away? FLA does not lack tourist opportunities for other things to do.

7. I wouldn't purchase the meal plan with your tickets.

Good luck. I'm sure you'll have fun. And if you're looking for less crowded times, my favorite time to go is Sept. and Oct.--great weather (albeit risk of hurricane--we were there for one while I was pg), and so much less crowded."