First project what should I look out for
The first thing to look out for is overplanning. This, along with overengineering, is even more true for your second project.
You have lots of ideas about how this program will behave, but don't get ahead of yourself. Remember what the problem is you want to solve, and try to keep focused on the simplest way to solve that, without tons of options or cases. For example, in its simplest form you want to programmatically add a calendar event, so create a simple html form and the simplest possible back-end to take the user input and add it to a calendar.
Don't worry about HIPAA up front, as you're going to make lots of security mistakes anyway, it's better to focus on the functionality for now.
Also don't worry too much about the interface, because you're going to decide this version sucks and you need to throw it away at some point. Then (and not a moment sooner) will be the right time to think about the interface, json vs. soap vs. web app, etc. For now, just start building the thing and prove that you can provide the value you believe this will provide.
I want to create a program that will take user input and create a
calendar using the input.

example: John,Conner 1/3/10 birthday  

This information will also be sortable by the obvious: last name,first name, date, (other).
It will be able to print this information as a list or a calendar.
It will have to have exceptions like 1/3/10 is put on the 2nd
(because the 3rd is a sat and weekends aren't usable dates)
Security is a must as its HIPPA information
Possible will be only used by myself on a work computer... but i would like to think others might use it eventually

I'm new to programming and have the following under my belt:
Learn python the hard way 
How to think like a computer scientist learn python 3
python for informatics
Given what i know the programming part of this doesn't really worry me. I feel like i have done similar if not more difficult things already. with the exception being the user interface setup... err the graphical part the user see's. I don't know how to set that up at all. (i used turtle does that count?)
Limitations:
I'm not sure what the computers at work are running. If its a server that the computers boot into or what. They are using Internet explorer.
So... i have researched some points i know i need to plan ahead about such as: 

GUI vs web application. --- i'm learning towards web application because I like the eventually seeing something i made get used on a more widespread basis... also i hear that GUI's area a pain. With this in mind i was going to learn Django.

But as a newbie i feel I might be sailing into a storm of things i haven't envisioned. And while i understand trail by fire is a good way to learn i feel it also pays to seek advice as to limit yourself... especially when you work 9 to 5 like i do.
So after all my to do. Is learning Django a logical next step for my I have in mind? What else might i want to consider..? finally maybe stackoverflow isn't the right spot for these types of questions! if so, where?