I used it this month with no problems at all. Both parks had very low attendance every day I was there. Wait times were 15 minutes or less for just about every attraction except the new roller coaster.
I would make sure Crush's Coaster is my first ride. Depending on how crowded it was I might stop at ToT for a fastpass, or after coming off of Crush get a FP for either RnR or ToT and get in line for the other.
http://www.disney.co.uk/usa-resorts/waltdisneyworld/VII/maps/pdf/wdwmap.pdf
http://www.kingdommagictravel.com/disneyworld/maps_index.htm
These are not as detailed as an ADC map, but I think they have all the major roads covered.
Credit disneygirl76 for this very extensive snack credit link:
http://www.associatedcontent.com/article/1539859/get_the_most_out_of_your_disney_dining.html?cat=16
Some (all?) of the Disney hotels have a front desk safe. I don't know the particular laws for Florida, but most hotels are not liable for things stolen from the safe in your room. On the other hand, they are liable if they disappear from the front desk safe. If that ring has value, you might...
I've traveled to a lot of places and thought I never would see the day, but for this same situation I used a travel pouch. After I got through security I put the ring in it and I never had to worry about losing it in my pocket.
http://forums.wdwmagic.com/showthread.php?t=313944&highlight=upgrade
I can't remember ever getting an upgraded room at WDW. DLP offered to upgrade us to one of their nicer hotels and when we declined they upgraded our room.
In the itinerary above, you have one weekday afternoon, two weekday mornings, and a weekend evening at the parks. In my opinion, one and a half weekdays is plenty to see everything at DLP, with time to do your favorites more than once. You're also spending time traveling back and forth from...