OK here's my 2 cents.
Why buy a digital camera at all??
You have been shooting film for years and have some great images in your gallery all shot with film! Use your film cameras. Learning digital takes time and it's easy to forget things that you would not normally need to think about on a shot by shot basis (ISO springs to mind).
Regards equipment my basic setup is as follows..... Work out the cost yourself. I've also added some tips on what you should think about.
20D
XT (2nd body and backup)
Zooms - You need 17-200 coverage over 2 or 3 lenses. If I was to choose again I'd have the 17-55 f2.8 IS and would still use the 70-200 f2.8L IS
I use the following
Canon 10-22 f3.5-4.5 - (Used for creative wide angle shots)
Tamron 28-75 f2.8 - Fast zoom for use in church and as a backup for the 24-105
Canon 24-105f4L IS - My preferred formals lens for groups
Canon 70-200 f2.8L IS - Fantastic all-rounder and always on one of my cameras. Church, formals (particularly single portraits), reception - amazing!!!
Primes - You need at least 2 fast zooms for dark churches, receptions and low evening light use without flash. As your weddings are outside this may not be so much a priority but will help later in the evening when light is low.
I use the following
50mm f1.4 - You can also look at the 50mm f1.8 - canon's cheapest lens (and a great one)
85mm f1.8 - Another great portrait lens.
100 f2.8 Macro - Use this for detail shots of the cake, rings, flowers etc. Also a great portrait lens in good light.
Use of flash I try no minimise however in bright light outside you may find dark shadows very difficult to live with. Use of a flash that has high speed mode will really help and you can add just a pop of flash to lighten these shadows.
The canon 580EX flash is probably a must have item - preferably 2
I also use a Sigma 500DG super as a backup flash but it's not as well built or easy to use as the canon.
Diffusers - Sto-Fen or a fong will help soften the light from your flash. Everyone has different ideas on the best. A cut off milk carton taped to the head works amazingly well!!! Buit perhaps you don't want to look that daft
I now have 8Gb of CF memory (very easy to shoot this amount) and I have an Epson P-2000 for backup. Laptops are too slow and while you try to use these for backup you are missing shots. Think about hiring an assistant for the days (a wife/friend etc) who can backup for you and carry your gear. I also have other lenses like the Tamron 17-35mm f2.8-4 and the amazing Canon 300f4L IS - I don't use this at weddings though and use a 1.4 converter if I need to be close and have enough light.
Depending on the situation, you may also need a decent tripod as well.