
Okay, my top five consecutive dates would be Sandra Bullock, Jennifer Anniston, Kiera Nightly, Natalie Portman, and Mila Jovavich.
I've done solo trips in September, October, and early December.
My favorite time of year to go to WDW is the end of October, through Halloween. The Food and Wine festival is happening, the weather is warm enough for swimming but not humid, rainfall is low, and hurricane season is over. Crowds are moderate to low, far lower than the summer season, and rates are Regular season. If you have an AP, there are usually some Passholder discounts available. Air and rental car rates are usually pretty cheap, too.
Second on my list would be September. It's hot, it's humid, and it's the middle of hurricane season, but September holds the twin Holy Grails for WDW fans - low crowds and cheap rates. Crowds are almost non-existent in September because of the tripple-threat: anniversary of 9/11, hurricane season, and all the kids go back to school. Because of the low bookings, rates in September are Value season, which is the lowest, and September is the most likely time of year for Passholder discounts and general public specials like free dining plan or ticket upgrades, or in years past, resort discount codes. Drink lots of water, carry a poncho, and walk right onto just about everything.
Third on my list is the first or second week of December, which I have done now for 3 years running because of MouseFest. After the Thanksgiving crowds clear out, crowd levels get very low for a couple of weeks, but the holiday decorations are up,
MVMCP is in full swing, and resort rates are in Regular season, but again, there are often discounts available either to Passholders or sometimes to the general public. Air and rental car rates tend to be pretty low at this time, and off-site hotels runa lots of specials because it's still considered off-season. And then there is MouseFest, but that's a whole 'nother topic.