Hi, and Welcome!!
First off, I would say, do yourself a BIG favor....take the Harley Rider's Edge riding course....yea, I know there are state classes you can take for $50 or so. The RE classes are typcially MUCH smaller and the instructor's are very familiar with big cruiser bikes, and they provide great pointers during the class related to them. After you learn to properly use the friction zone under various circumstances, and properly navigate the "quadrant of death", you will be ready to ride any bike.
Secondly, get the DVD "Ride Like a Pro". Jerry shows you how anyone can handle even a gigantic police bike, in low speed maneuvers with ease and confidence. I watch this DVD at the beginning of each riding season, take my cones to a parking lot on a weekend, and do some of the exercises.....riding a bike is dead serious business, and practice in off-street conditions helps me to keep my skills sharp.
I rode dirt bikes, like the OP, when I was younger. Decided to get back into motorcycling in 2008, and took the Harley class. Expensive but WELL worth the cost.
My first bike right out of the gate was a 2008 Softail Custom....
I bought the one I wanted as my first cruiser, and taking the RE class had me fully prepared to handle it with absolutely no issues.
The Breakout is a VERY low bike so riding it is actually very easy. It inspires a lot of confidence as soon as you sit on it because virtually everyone can hold it up, flat footed, easily. The bars come back to meet your hands giving you an upright, comfortable riding position.
As big bikes go, the Breakout is light(comparing it to all of the Harley touring models that take a good deal of practice to figure out)
The wide rear tire takes just a little getting used to, but it's a minor detail you will figure out right away....