I second what Tim is saying here. I personally started my longer trips by increasing mileage, time, and intensity bit by bit. I started with a 5 hr round trip and quickly discovered I needed to do something about the brick I had for a seat on the CBR(padded bicycle shorts were the cure and continue to be). Then I started taking multiple 8 hr round trips to SEO and into WV. Once I set my sights on a trip to the Gap and mapped out at least a 10hr ride to get there, I put together a 10hr round trip that included rt555(I didn’t know of better roads at the time). Around that time I started lurking on this website and found better roads from posts and just kept riding more and more. Then to truly prepare myself, I rode 2 near 500 mile days back to back. The following year I made my solo trip and loved every second of it. I will admit this is probably a reflection of my personality. I’m a planner and a bit of a loaner. I personally have never done the OR thing at Deals, but I have participated in some Epic rides and other group rides. Every time I have participated in an OR ride it has been good times and I have met great people. @flashesbuck my guess is there will be a spring Epic ride again this year. My suggestion would be show up for that and use that as a basis for your decision.