You can totally have from WDW and DLR on the same CD account. I know have almost 1200 of my own (with edits/enhancements) from both. Add I'm planning on at least 2 more trips to DLR before I have to order my CD. I was able to get 30 extra days to order by ordering one thing from the site (I picked the cheapest, stickers-$12.99 inc. shipping) which gave me those extra 30 days.
The price you pay for the CD is based on the
last card you load. So, if you load your DLR last, the price will be $59.95. This is a better deal than pre-ordering the CD for WDW.

If someone is your group is going to WDW last, then I would suggest someone keeping a PP card from DLR with a few pictures on it and up loading that card last to get the better price-whoever is paying for the CD should handle this. So your organizer should make sure that a DLR PP card is the last loaded card. Otherwise you'll pay $129.95 (or $99.95 pre-paid)
And the good news I heard Tues (10-14) is starting this week (don't know if it's Sunday, or ???) PP photogs will be taking pix of you with Jack and Sally and the hitch hiking ghosts enhancement will be back. Apparently, Tim Burton came to an agreement with Disney ($$$$$

)
If you have any questions ask, I'm becoming an expert at PP. Where are the enhanced ones, how do you get Darth, etc.
Always let the PP photog know you are buying (or pre-ordered) the CD and that they can take as many pix as they want. You can even suggest a few. Have fun-I find it almost addicting to try and get as many PP taken as we can. My family can't wait until I order this CD so they don't have to take any more pictures

. I have a suprise for them-I plan on doing it again for the holidays (sometime after 11-10 which is when my current CD has to be ordered) My DNephew will be in this years Christmas parade so I know we will be going often.
Remember, you can
get up to 60 days from the date of your first picture 'til you need to order. For example, say you go to DLR starting Dec. 1st. You'll have until Dec. 31st to upload those pictures. Then you'll have another 30 days to order them. (Jan. 30th). If you upload your pictures when you get back (say Dec. 10th) then you'll only have until Jan. 9th to place the CD order. the current promotion of gettting an extra 30 days ends in Nov. so your Dec. trip won't comply. Unless they extend the offer.
I organized a small (3 family) CD share for WDW. I wasn't sure about the DLR pricing so I based our swap on the $99.95 prepay price. Once I get the CDs and burn the copies I will be refunding my 2 participants some $$ for the cost savings. I will be able to get my prepaid amount refunded.
We had a few small problems with our little group but most were solved by Guest Services at PP, easily. I, stupidly, used a card from last year (one of those smaller ones from the water parks with a bracelet attached) without thinking that I had used that card on another account. (last years CD share-which I didn't organize). Also one of my share thinks one of her family uploaded her card to a different account because when she tried to upload it into mine it said the card was already used under a different account. Guest Services was able to transfer both cards to my account.
There were 2 things that they couldn't correct. Several of pix from WDW and DLR had double enhanced images (2 Simbas, 2 Stitches, etc.) Once the images are on the photos they can't remove them. I think I can edit them off with Photoshop. Also, 1 picture at DHS and 3 pix from DLR were missing. PP said they couldn't find them either "equipment failure". So if there are some picture you really want to make sure you get, stop at Photo Supply (DLR) or the equivalent at WDW, to make sure they are there. If they tell you they are working on them and they will show up later, check back. We didn't and my Hook pix never showed.

Looking at your pix at WDW or DLR will not start the 30 day clock ticking.
HTHs.