On Wednesday, I sent in the paper work for the Iron Butt Silver National Parks Tour. My wife, Nina, and I did it two-up on a 2010 Bonneville T100. We didn't get bored, but we spent very little time on freeways. It was kind of time consuming, but chasing visitor centers at national parks, memorials, seashores, battlefields, etc. ended up being kind of rewarding -- and tiring. We've now ridden two-up through the 48 lower states and one Canadian province, but it took us 35 years.
I haven't gotten bored on a motorcycle yet. I guess I'm still concentrating too much on figuring out how to ride them better to give boredom much opportunity.
About twenty years ago, I had what looked like a good opportunity to go for a thousand mile day. I was headed home to Washington from Colorado. Maybe 100 miles from my goal, very early in the morning, the headlight on my BMW K100RS started going out and coming back on. I pulled over and slept in the ditch. When it got light, I rode on home. A day or so later, I pulled the gas tank and pushed on the relays. The load shedding relay clicked down. Somehow, after many, many miles, it pretty much unplugged itself.
I'm thinking you are probably ready to give it a go. Whether you succeed or not, you still get to ride your motorcycle. And one nice thing about the Iron Butt rides is that if you don't make it, no one has to know.