What about 2 (or 3) of you flying and the 16 year old taking the train? A roomette is a small space for a 4 year old. My little guy was 4 on the auto train last year and we had a family bedroom, and after our experience on it we've decided that the wife and kids will fly home, and I'll take the AT alone.
Also worthy of note is how the train is frequently quite late. 21 hours could easily turn into 24 or more....
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Yes, this...honestly I would not even consider this as a viable option. No way in the world would i pay double the price for an at least 7x longer journey to WDW and then to have to pay for transportation to the resort as opposed to taking the ME and having to now take the car seat. I just can't imagine any scenario in which this would ever be a consideration. I mean I guess if you just really really wanted to ride a train to Disney and were willing to pay a very expensive price, but man seems crazy.
As others have pointed out why not just drive? I hate road trips and it would never be my first choice, but if flying is just totally not a possibility, then just save yourself the trouble and money and drive.