Hello again-
I was the same way when we were initially planning- I wanted the traditional Saturday wedding. We would have met the requirements either way. But, we changed becuase MIL will be retiring in the spring. We thought it an unecessary burden to have the wedding right at that point. They're both teachers, so we were a little bit limited on the dates and times of year we could seriously look into. We chose December 29, 2005. We met at Disney December 29, 2000. You can probably do the math and figure it out
It was a Thursday and we had no questions from anyone that was a part or invited to the wedding. You will always have naysayers and party poopers on the outside who will try to cast judgement. Don't let them rain on your parade. Ever.
Currently, the MK photo shoot is $800 plus the cost of having your hair and make-up done (if you choose), the tuxedo rental for him, and your bouquet (if it will need to be redone). There are fees associated with paying for your photos, as well. If you do not need this to meet your minimum expenditure, you can have it done up to one year later. We have gone this route as neither of us wanted to be getting up for a photo shoot after 2-3 hours of sleep. If you need it to meet the minimum expenditure (for a custom), then it must be done the day of the wedding or the morning after. Again, I am unfamiliar with the rules in the intimate weddings department.
I ourhcased my dress at David's Bridal. You can begin looking at the websites for the designers, etc., now. I wouldn't get anything just yet as designs and styles change. I had a girlfriend but her dress when I did. Only problem is that her wedding was 18 months away when she bought it. Of course now, she doesn't want to wear that one. I tried to warn her...
For an intimate, you will need to have one of the girls answer the question concerning the dinner. I know Disney has gotten much stricter about this. I woul dnot plan on having a catered meal at Disney if you're planning an intimate. In all likelihood, they will cancel it. It is as though you're trying to get the perks of having a custom wedding, but paying the initmate price. I believe one of the girls had her event cancelled by Disney catering when they learned it was in conjunction with a wedding. You will need to speak directly with you Event Manager when the time comes. Until then, I leave it to the intimate brides to explain this one. Custom brides usually plan a whole, traditional reception.
Traditionally, airfare and hotel accomodations do not fall within the responsibilities of the bride and groom, but rather the guests. If you are booking rooms and paying for everyone, I would take the cheapest thing available. On property, obviously one of the All-Stars or the Pop. Maybe you can find a better deal off-property. Or, Coronado Springs might offer a good group rate becuase they have the conventions. Is this something that you absolutely have to do? Or is it a kind gesture? If it is a kind gesture, select those individuals that will be unable to attend unless you pay their way. I wouldn't make it general knowledge either. We paid for a lot of the things for my BMs (3 of 4 wee family) and my grandparents.
Something to consider: For custom brides (and I have every reason to believe for intimate brides, as well), you can block rooms and receive a discounted rate on the rooms for your group through the Fairy Tale Wedding Department. If you carefully choose one of the "value" or "regular" priced seasons, the prices on the room could be considerably discounted from the regular rack rates. As a DVC member, you may be able to use your points for a number of family and friends to stay. I believe Janet2K did this for her vow renewal.
Disney may or may not accept payments. Your best bet is probably a high yield savings account. You will have a $1,000 deposit made to reserve your space and time. This is sent when you return your signed contract. After that, payment for your event is due one month before your wedding. The $1,000 deposit is not counted towards the final payment in any way. It is returnable, but only after the event. It is held in case there is damage to anything you rented, you no-show, chage your mind, etc.
As far as having it sooner- check into the prices for off-site vendore for photography, videogrpahy, floral, etc. I was exceedingly hapy with Disney's Photogrpahic services... after I unsuccessfully tried to back out of my contract with less than 30 days. Many of the girls here use Randy Chapman. His rates are very reasonable and his work is excellent. Videogrpahy favorite is STVS. I am unsure on prices. Floral- again, I used Disney and was thrilled. I was using flowers from Whimsical Wey as my inspiration. I found out they were Orlando-based a little too late! There are a lot of florists around. Check them out.
Do not forget to budget for allt he add-ons. They add up quick and can ruin you if you don't remember to allot for them. They include hair and make-up, nails, hair coloring before the wedding if applicable, massages, tanning, tuxedo rentals, alteration costs for your dress, steaming for your dress the day of the wedding (Carolyn Allen's boutique), floral preservation (allot a lot if you look into doing this), any costs you might be covering for your BMs, gifts for parents/attendants/each other, rehearsal dinner costs, officiant fees, tips for vendors, food and souvenir money for your visit, accessories for your wedding day attire, any DIY projects for the wedding, money to purchase photos after the wedding, etc. They just seem to keep adding up!
Link to my wedding photos:
Click here
Where did you have your guests stay? I'm a dvc member and will most likely use some of my points for the guests. The 20 people would include my dh and I. I definitely want the cinderella coach! 
