I am a single mom with an 11 year old son. We travel alone to WDW at least once a year--our next trip is in 30 days! (August 15-31, WDW,
DCL and Universal). I find our trips to be a great time to reconnect, after all the craziness of work/school/sports etc throughout the year. This will be our first time on DCL, and I'm sure my son will like the interaction there with the other kids, but I find one of the great things about Disney is I don't feel awkward traveling alone with my child, we both have so much fun and most people are so friendly (on the buses, in lines, etc.). We always end up meeting and talking to other families and my son always finds a friend his age at the pools to play with too. To the OP, I wish our trips were overlapping, I totally would be up for coordinating a meet!