I've taken two or three trips down to WDW by myself. I always end up staying at the All Star Music so I can save money on hotel and spend it on food and shopping (besides, I like ASMu). On one of my trips, I was going to be arriving at about 8:00 PM and knew that all of the nearest available rooms would be taken by the time I checked in. A couple of days before my trip, I called the room controller and explained that I was a woman travelling alone and checking in late, and could I please request a room relatively close to the main building for security reasons? When I did check in, the desk clerk was so suprised by my room location that she commented that I must know some important people. I don't usually make room requests, but in those circumstances it was worth it to me to not have to walk through a dark hotel complex every night.
One thing I did before my first solo trip was take myself out to dinner so that I could get a feel for the whole "table for one" thing. A lot of people suggest requesting a counter seat to feel less conspicuous at restaurants. I'm not a fan of sitting on a stool with my back to the room, though. I always request a table. Usually, it's a nice little table for two and the wait staff remove the other setting without a word. I've found that dining at slower periods usually nets me better service. The CMs are almost always friendly and take extra time to talk to me, which is nice. I've only ever had one bad dining experience at WDW.
