Hello wendesigneu,
After looking at your project, I have to say that it is quite easy, I have delivered many Add-Ins with features like the ones you request, these are actually very common. I am an IT Engineer and I work exclusively with Outlook Add-Ins.
Most Outlook Add-Ins usually contains communications with external sources (applications, servers, databases, etc). This communication may be to upload or download data to or from Outlook. In any case, the solution is practically the same and I can surely help you with your project, so you can get the best results out of your requirements.
BTW, in your project description you mention something about the Outlook compatibility, and includes a range from "2000" to 2013, did you mean 2000 or 2010? In case you need compatibility with very old Outlook versions, I could use Add-In Express to get those versions at an additional cost, and I think it would get as far as 2003. I think that with Outlook 2003 would be more than enough.
Well, let me know your thoughts if you are interested.
Regards.-