Last year, first time, I went mid to late August. The free dining plan coupled with a Huge sale at southwest, well, I could not turn it down.
PRO's - This disney trip cost me about 1/3 of what our other trip cost.
- FREE DINING PLAN - this was so awesome, I loved it! Ate like kings and tried places we could not before. Late August through September Disney usually offers big discounts in order to tempt people to go!
- NO CROWDS - grant it, I was using TGM best days, but even still, being able to walk on to space mountain at 2 pm in the afternoon, well, that was spectacular.
- Using the free dining plan, we stayed for 10 days instead of a week. Why? because each additional day only cost us the rack rate of a moderate in value season and an additional ten bucks for the ticket. I can rationalize anything, but that was like pay 130 bucks a day for 3 days for hotel, food and tickets -- thats a good deal to me!
- Getting my room request -- I got the most perfect room right beside the food court! This could be just luck, but also, with less people there was a better chance for me to get my room request
- Easy transportation -- never had to wait for a bus at ALL! I think I stood only once in 10 days, and that was after Fantasmic when we exited with the masses.
- ME worked perfectly for us! Again, low crowd levels probably made this such a positive experience.
Cons-- it is humid! But, never once did it make me feel at all bad, because we used the TGM philosophy (parks early generally, afternoon breaks at the pool, then evening fun <-- dont think that is divulging anything specific, am I?) Swimming was a welcome treat, you obviously never had to worry about it being warm enough. (so only a sorta con for me -- as we found it no problem, but I can tell you I was worried about this before I went)
-- Worried about the start of huricane season. Worried about having to cancel due to hurricane. This was a big one. I had cancellation insurance, and kept my fingers crossed. Either you decide you can live with that worry or not.
Now, I have no idea if the free dining plan will be offered this year, but I tell you if it is -- I will be on the phone at 7 a.m. the morning it is released!
I hope this helps, and again, this is just my personal experience,, YMMV.