I have gone solo to WDW 5 times and have 2 more trips planned for next year. I have to admit that I have never had a CM laugh at me when I made ADR's though. I typically get "Wow, I would love to be able to travel solo or I'm jealous." You can make ADR's online too (which is what I did for most of mine). Also, if you are unable to find a table with a party of one, try a party of two. It is amazing how many tables suddenly appear.
I love the freedom that comes with going solo. You get to go where you want, when you want. Eat where & when you want. Ride an attraction 10 times (my fave is the Haunted Mansion that I rode 15 times in the week & a half I was at WDW last November) or skip one all together (I don't do coasters, so Space, Splash, ToT, RnRC & EE are all out for me). You get to relax and know that the only person you have to be concerned with having a good time is yourself.
Some of my favorite places to dine are:
Crystal Palace
Rose & Crown
50's Primetime
Via Napoli
Artist Point
Whispering Canyon
Flying Fish
Citricos
Beaches & Cream
Yachtsman Steakhouse
Le Cellier
California Grill
Boulangerie Patisserie
If you are going during the Food & Wine Festival, some great food is at Australia, Canada, UK, Italy & Germany, although we had some good food at some of the other "countries" too. The lamb chop at Australia & Salmon in Canada kiosks were AMAZING!!!