Boy Scout motto: Be Prepared! I have averaged at least once every 500 miles or so of someone pulling out in front of me. Speed of an oncoming bike can't be judged by most drivers due to smaller mass of it.
Speaking from what is now experience...learn to use front brakes. 2 years into riding...
I've had them do a couple of regular services and had them install new cam in a soft ail about 2 yrs ago. I will say the father that owned/ran/built drag bikes passed away a year plus ago. Not sure about services/customization after he passed. Folks have differing opinions. There is a motorcycle...
$600 plus for a windshield is ridiculous. Get out of the HD shop and go aftermarket. Check out ebay, J&P and hundreds of other online stores. As far as the windshield goes, you can get a full batwing fairing with a killer bluetooth stereo and polk audio speakers for ~$750 from Reckless Motorcycles.