To start this off I feel that it's important to say that for the past couple of years I have been working in an environment that most people would choose to avoid.  But by living through this I have learned some very valuable and interesting tricks that I am trying to transition to the new projects that I am working on.  I am still very new to working with DNN so there are still some learning curves that I am trying to find my way around.  But here are a list of items that I am working through, If there are any thoughts on these subjects I would be really excited to hear about them.

1. Multiple server deployments with DNN - since there is so much that it tied up in the database for working with DNN I am still trying to figure out if there are any best practices around working with a development environment and a production environment.
2. Data - Data seems to be a really sensitive subject inside DNN in the fact that the structure of the database seems to be much less complicated that say... WordPress.  But there are still weird and kind of silly paradigms that you have to fit yourself into to make things work.  The whole self referencing tables is getting a little old.
3. Convention - Some of the things that you have to accept to be able to use the software seem more than a little silly.  The upgraded ORM framework seems really under powered compared to many of the options that are on the market.

With all of that said I realize that there is a huge user base out there that is currently making use of the product, and they wouldn't all be there if there wasn't a reason.  I am still working to that point and hopefully I will com to understand why everyone talks about the power of DNN.