we stayed off site for the first time last September at Windsor Hills. Having the space was incredible and the rate was killer $199 for a week in a 2/2/ condo. We for sure missed the ease of staying on site but really liked getting to stay longer due to the great rate more, lol. With a 2 year old, hmmm., they are young enough at that age to be stroller~able and you call the shots for the most part on timing of things so that would be no biggie (like not being controlled by a certain FP time for a princess M&G) I wouldn't say it's particularly difficult to leave, just add in time for hiking it back to your car. The lots aren't really bad to get to except MK and if you are lucky to get there early enough you may not even need a tram for there. We used the tram once at AK and qonce at MK...then decided walking was more efficient in more in our control. We weren't patient enough to sit and wait for the tram to fill before leaving, making it's stops etc. Now the traffic to/from the condo was not something we liked all that much, and if we go back I think we will do a split on/off...3 solid on site nights at the beginning of the trip and then a week prob back at WH. Many like Bonnet creek as it is so close. We are commando park goers tho, and now 4 adults so we do pack a lot into our days. Honestly it is really hard to say until you just take the plunge and try it off site, but maybe try a split stay for the best of both worlds?