Hi RighteousssCrush, thanks for sharing your experiences! Most of my comments will be in line with what others have shared, but as a self proclaimed "expert" solo traveler I just had to add my 2 cents.
So let's start with the Pros. There is nothing more awesome than being entirely in control of your Disney experience and itinerary. I spent so much time in shops, trying new snacks, enjoying parades and shows, and re-riding my favorite rides multiple times. There was no rush, no meltdowns, and my face actually hurt from smiling so much on the rides
First, I'm glad to hear you had a great trip! One of the main benefits of going solo is doing exactly what you want to do, whether that is ride every ride or stop and smell the roses.
Ok now for the Cons. To be fair if I did a solo trip again it would be just as short, and I would apply the changes I noticed would help. In my opinion dining and transportation were the most awkward for me. Mind you I am a shy personality and so some people would not deal with this (but it still deserves to be said for anyone out there like me).
My solo trips to WDW have all been the short duration as well, usually around 3-4 days. Orlando is only a 2 hour direct flight from Nashville so that makes it very easy. Usually if I'm planning to stay a week or longer then I'll have family or friends with me.
I likewise felt awkward being alone on those transportation buses to the parks. I got similar speeches from those bus drivers. One bus driver lady said to me "Is it just you all by your lonesome self?" To which I laughed and said yes but I was excited to go ride my favorite ride splash mountain, she smiled. If I had rented a car I know I would have zipped between parks and avoided a majority of my awkwardness in those situations.
Usually I will rent a car when visiting WDW, because good deals can usually be found if you're not going at a busy time (check kayak.com, priceline.com or hotwire.com closer to your trip). The time saved is worth it for me (especially if I'm going to Universal from Disney property), but I understand it may not be to someone else!
As far as comments from cast members, I don't remember many comments about me being solo with the exception of dining. Maybe it's more common for a guy traveling alone vs. a girl traveling alone - so that may be why I don't get many comments. I've heard a lot of people, if they notice you are solo (I think less people notice then we really think), just think you are separated from your party for a bit. I don't think CM have bad intentions, they just talk before they think sometimes like all of us.
Dining can be awkward, especially the "Just one?" comments, but it's not uncommon for me to dine solo back at home if it's somewhere I really want to eat at.
I'm introverted, so at the end of the day I need my "me" time to recharge (maybe that's why I enjoy solo trips on another level - be at my happy place with just my thoughts). But at the end of the day, I still crave social activity as well. So I talk to CM's at every opportunity. Ask them how their day is going, etc. I also do the same in lines - it's really easy to tell if someone will be open to having a conversation with a complete stranger after a few words. I basically just try to be positive and that tends to work out well for me. Just because you're solo at WDW doesn't mean you're "alone".
Again, I'm sure all this has been touched on but I really wanted to share my experiences.
