@midtown
If you really want to expand your riding ability there are a few classes I've taken over the years.
I should clarify that I got an exemption in Texas with a motorcycle permit at 15 and own a CRF250L, Ninja 1000 that I've ridden from Austin to Sturgis, Yellowstone, Glacier National Park, and on to Seattle before having it shipped back to Austin as well as a YZ250.
One thing that will up your riding game is learning off road basics. They teach this class at a location outside Atlanta. I'm sure there are other locations too. The one outside Atlanta has off-road bikes you can use for the class. (Or it used to)
https://msf-usa.org/start-your-ride/dirtbike-school/
There are also follow up courses available. I've taken one for off road but not the others. However, I'm confident it will greatly enhance your capabilities, and I suggest taking all of them that you can and confirming if they provide a motorcycle if yours isn't suited.
https://msf-usa.org/advance-your-ride/
Finally, if you've taken all those and want to move your skill WAY, WAY higher California Super Bike has a 2 day class where they provide a BMW S1000 and 2 days of track school. You'll learn more in those 2 days than you will in several years of riding. Things like, entry point, apex, exit point, trail breaking, entry speeds, just so, so much. It is NOT cheap, but you'll be a very different rider on the other side.
https://superbikeschool.com/
If you have questions on gear, I own more than I care to admit. Happy to provide feedback in as much or as little detail as you like.
On insurance, Progressive is one of the better motorcycle insurance companies, but I suggest shopping every couple of years.
Edit - Because pics or it didn't happen