Let me see if I can help (and please someone chime in if I am wrong)...
1. I didn't use Disney photography (except for my MK shoot), but you aren't guaranteed who you request. You can put in a request (and obviously the earlier you put in the better), but I don't believe that Disney will DEFINITELY give them to you...if that makes sense. The person may have another wedding, be off that day, etc. However, you can make requests.
2. Only services that take place on the day of your wedding count towards your minimum. I believe I was told that the only way the MK session would count would be if it was on your wedding day.
3. I'm not sure about the staying offsite thing for the portrait session. The only thing that throws me for a loop would be that your photographer picks you up for the session at your resort, so I don't know if they would pick you up if you stayed offsite. Maybe you could meet them at a resort? Someone else may be able to answer that one...
4. I'm sure that if you wanted Randy to take some photos before your wedding outside of the park (I'm assuming that you are having the wedding inside a park?). If you are having your wedding outside of the park, I have heard of a few brides that used both the Disney photographer that was included in their escape package as well as hiring Randy. That way you have pictures from both. I believe you would just have to ask Randy's permission - and I think that brides that have done it have said that Randy was fine with it. We had Randy shoot our wedding and he is awesome.
I hope that these answer your questions, and maybe someone else can answer the ones that I'm not sure about (and correct anything that I may be wrong about).
Good luck!!!
