Possibilities within CMR 2011 - dynamics-crm-2011

Consider the following requirements for CRM 2011:
2 custom entities are needed, let's say EntityA and EntityB.
EntityA contains the following fields:
ContactA (lookup on contact)
ContactB (lookup on contact)
Customer (lookup on account)
EntityB contains the following field:
Beneficiary (lookup on either contact or account)
A button must be added to the ribbon of the form of EntityA. When clicking this button a dialog must start where the user can make a selection wether to use field ContactA, ContactB or Customer. When the selection is made and the dialog is closed, a new EntityB must be created and sets the value of field Beneficiary to the value that is selected in the dialog.
Also the form of EntityB must get a new button in the ribbon. When this button is clicked a report on the report server is executed. The report must not be shown but instead a PDF must be generated that has to be attached to an email activity and the email must be send to the beneficiary.
I'm afraid that not all requirements are possible in CRM 2011:
Is is possible to create a lookup on 2 or more entities (like OwnerId that can look up SystemUser and Team values)?
Is it possible to start a dialog from a ribbon button?
Is it possible to use values from an existing entity in a dialog?
Is it possible to instantly generate a pdf from a report to add it as a mailattachment?
The CRM environment is partner hosted, but CRM is not sandboxed and local resources can be used.
An other option that comes to mind is instead of creating it all in CRM 2011, to create an external webapplication to overcome some of the bottlenecks. Would this be a possibility or is it just a bad idea?
Thanks for your advise!

Is is possible to create a lookup on 2 or more entities (like OwnerId that can look up SystemUser and Team values)? - Answer: No. Check this link. But you can solve this with two lookup fields and one option set which will be filter field.
Is it possible to start a dialog from a ribbon button? - Answer: Yes. You have a lot of articles on this topic.
Is it possible to use values from an existing entity in a dialog? - Answer: Yes. You can use values of selected entity, for which you are start dialog. Also check those links for creating dialogs.
Is it possible to instantly generate a pdf from a report to add it as a mailattachment? - Answer: I don't have experience with this, but some articles says that it is possible. Check this two posts.
I hope this will help :)

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If you just need to show the value you can create a Quick View Form and put it on the form.
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As for auto-filling the property fields, I suggest you check out this post that explains how to auto-fill properties when document is added.
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