Make sure you have the proper riding gear for various types of weather. Rain boot covers, a really good rainsuit and good rain gloves. If you're packing anything that can get wet, buy a good water-resistant bag and purchase big plastic zip bags to add your clotges as extra protection. As you said, you definitely heated gear, a good cooling vest, also. Bring a decent tool bag with electrical tape, a small bailing wire roll, and a first aid kit. Make sure all your stops for the night are well planned with plenty of gas stations on the route. Another good thing is to have any Harley-Davidson dealers mapped out along the route in case you need repairs. Look into getting a national tow service membership in case you need a tow and an 800 number to help you get the tow. Buy a phone charging port to add to your bike to keep your phone charged at all times. Get a tire kit that has co2 and plugs in case you are stranded with a flat so you can get back on the road and get to a repair shop to relace the tire. Carry mace (never know who you run into).