It's fair to say I over-prepared for my ride from Virginia to Sturgis this year. Heck, I even went to the extreme of buying another motorcycle just for the ride, but I'll use any excuse to get another Harley, so I'll rule that out. This is about things that worked well, things that were a bust, and things that fell into the "It seemed like a good idea at the time." department.
What worked well:
Reda Gas Container - Though I never once needed it, that Reda 1-gallon gas container provided peace of mind on two occasions, and I was damn glad I had it. Gladder still that I remembered to put gas in it! (thanks to Chuck for the reminders!)
A bike with a fairing - This falls under the bike purchase, sorta, but I did long ride on a Softail Custom with a detachable windshield and wind deflectors mounted, so I had an idea of a baseline for daily mileage. Having a fairing made the longer ride far less fatiguing, and gave me a longer daily range.
Saddlebag/Tour-Pack liners - I bought these liners a while back, just in case, and wow did they make my overnight stops easier. I just opened up the tour pack or saddlebag and hauled the liner, with contents, into the hotel room. No running back to the parking lot in my boxers to dig in the saddlebag for the toothbrush!
Powerlet 12V accessory plug, bar mounted - Kept the iPhone charged all the way up and back.
Harley rain gear - This Harley stuff may be pricey, but it works. Don't buy the cheap stuff. You'll just toss it and buy the good stuff anyway. (That's easy for me to say. My son and daughter-in-law gave me mine for a gift. Thanks Kenny and Debbie!)
New Metzler M880 Marathon tires. Great ride characteristics. I liked the way the bike felt with this tire design and tread pattern, and no worries on wet roads. And after the 4,920 miles, they still looked almost new, so these don't wear as fast as the Harley Dunlops.
Installation, while pretty simple, requires rethreading a hole in the control, by the way. Minor mod to the stock hardware. Hence my request to get the Kuryakn guys to slap it on. Hell for 15 bucks, how could I say no?
Remember that a Cruise Mate is a throttle lock, and not a cruise control. When using it, uphill sections mean you'll slow down, and going downhill causes you to speed up (like a fucking rocket), but this little deal is an outstanding, low-cost solution for giving your right hand a rest on long trips, and is a lifesaver on the long flat stretches. Like anywhere between Denver and the eastern border of Kansas....
I tried to get one of these Cruise Mates installed before I left Virginia, but I ran out of time and opted instead for a quickly-available and slightly-easier-to-install solution from eBay. See below.
Yes, I know I'm partially deaf, but even cranked up, I didn't hear much, while the GPS voice was SCREAMING AT ME. TURN, TURN, TURN!!!! That fucking woman drove me nuts.....
Scala Headset Pt 2 - I wasn't using the microphone, but the damn thing must stay attached in order to use the rest of the unit. It was always in the way. After a while, I just gave up on this thing.
Scala Headset Conclusion - For the trip, it was a waste of money, but maybe it'll be OK for riding 2-up, so I won't list it on eBay. Yet.
GPS SunShade - High expectations, but could barely see the GPS in sunlight, before or after installation. Left it on cause it was better than nothing, but don't get your hopes up. And as you can see, despite the pretty pictures on the internet, it's sorta ugly.
TomTom Rider 2 GPS - On this ride, I really didn't need the GPS, but it was a convenience, and saved me from a few wrong turns. That said, trying to look at it in the bright sun, while simultaneously trying to keep from being run over, also caused me to miss a few turns so......
I also found out that this particular GPS wouldn't let me store a campsite location since it wasn't actually on a road. I thought that was a little fucked up.
On one occasion, I did get turned around in the Black Hills and wasn't sure which way was home, but in the Black Hills, with all the scenery and riding a motorcycle, who cares? Anyway, the TomTom Rider 2 GPS helped get me home.
iPhone handlebar mount - Damn, who cares where your iPhone is while you're riding?!? I thought having it up there would be convenient and cool, but in reality, not much value at all. The mount was close to the 12V power source so I guess that helped, but the phone could just as easily been in the windshield bag. I sure wasn't checking Facebook or reading texts while riding,,,,
Saddlebag lid organizer - They were there but I didn't use 'em. Just something extra to dig through.....
So that's just a few thoughts on equipment for a road trip. There was definitely more good than bad, and maybe I could have saved a couple hundred, but all in all, no regrets except I can still hear all those pings, voices, and nagging reminders that were received loud and clear through the headset, yet I couldn't hear the fucking music.