First off, thanks for the suggestions, I'll be sure to add any that we can get specific wishes for into the appropriate product's bugbase as feature requests.
1. Image resizing and multiple image upload 
We are planning on having image resizing in the next version of Digital File Pro (DFP). Sorry, no timeline as yet.
You can currently upload as many files as you want with Digital File Pro; you would need to apply Digital File Pro once for each file filed you want to upload from. You could also loop over the DFP code if you wanted to work on an arbitrary list of form fields, but you would need to write the looping code and customize the DFP function to pass in the form field referenced in the current iteration of the loop. I do understand that that isn't automated, but at least currently possible if you can dig in a little into the code.
2. conditional regions behairvor similar to ADDT with other additions like show region if user is logged in, conditional region based on if file exist or filed exist etc
I don't have access to ADDT, so not sure what conditional regions it has available. Could you describe them, or even provide a link to a help page that lists out what you're specifically asking for?
SecurityAssist does have the ability to apply show regions based upon rules, a default rule created by SecurityAssist is a logged in user. So you can wrap a selection with a show if logged in, or show if not logged in. Rules can contain some custom code, so I suppose that you could extend them to check for the existance of a file, but you'd would need to write that specific one yourself.
3. More form controls similar to ADDT
Again no ADDT access, so please explain specifically what types of form controls you're missing out on in our tools.
3. More custom triggers and more development in this area
Please explain what triggers you'd like to see. Our current Triggers are fairly powerful for initiating the action of our server code, but there's always room to consider something useful. If you have a few sample uses and any code chunks would be quite useful if there is something that you find you need to do a lot of (or even what you find you're doing a lot of that you don't have ready solutions to are great as well).
4. Page and record navigation
We have thought about this in regard to DataAssist results pages. Do you have any specific suggestions that would be good to have some sort of automated solution for?
5. Improving integration into DW. I don't like that the different tools are all over the place as I have everything from webassist
We do put a good bit of thought into where our extensions are accessible from within the Dreamweaver user interface, but we're certainly open for improving the user experience. What specifically would be "improving integration" mean to you? DO you have some examples of what you'd put in a different/new place?
