I've soloed five times and can't wait to go again. I've stayed at OKW once (not solo) and been there a couple of times for dinner. The resort confuses me- the layout, the bus system, etc- so I'd recommend either being really familiar with the resort layout OR request a room close to the check-in/hospitality area. I have never felt unsafe on any Disney property... just make smart choices and pay attention to your spidey-sense.
I often eat at the bar in a restaurant. In general, the bartenders are very friendly and will chat with you as they can. Full menu is usually available. I have no problem sitting at a table by myself, just enjoy the company of the bartenders and other patrons (yes, folks at the bar are also good company).
TAKE BREAKS- even if you are staying in the park. I carry my Nook in my park bag. I like getting a bev or snack and people watching or sitting in the shade, reading, as a break. I find I will push myself too hard when traveling solo as opposed to when I am with others, and if I don't make myself take rest breaks, I'll burn out.
Don't be intimidated. MAKE yourself get up and go. If you go back to the resort for a late afternoon break, MAKE yourself to out for dinner or to DSprings for the evening. On my first trip I let myself get into the "oh it's such a long walk to the bus stop" mode and didn't use my time wisely; came home with regrets about things I'd missed. Sometimes it's hard to be self-motivated, but I've found that MAKING myself do something causes far fewer regrets than skipping things and staying in my room.
Talk to people when you are in lines. Most folks are interested in learning where you are from, why you are at Disney solo, and how it's working out. I've met some very nice people, been invited to join them for a drink or share a cab on the Skyliner, etc. Don't be afraid of strangers- because they aren't really, 100% strangers. You are all at Disney, so you already have a LOT in common!