Yay! Way to go. 
Re: riding with friends - On my first TOSRV I'd started out with a guy I rode with a lot, but I knew he was a little bit stronger than I. We got separated early the first day when he got ahead of me. It turned out that he had stopped at the first food stop - a detour of a couple of miles off the main route - while I had gone on, since I really didn't need any provisions so early in the ride. When we hadn't seen each other for a while, he started going slower than he normally would, trying to wait for me, and I was pushing hard, trying to catch up to him ... when he was behind me the whole time.
He was staying with some friends Saturday night and I didn't have their contact information, so I never saw him again the whole weekend.
This was in '83, the year they still talk about in the brochure.
25 mph headwinds all day both days. Saturday was the first warm day we'd had all year, 85° and bright sunshine. Sunday brought rain and a high of about 45°. I was miserable toward the end of the day Sunday - even though I'd stopped at the LBS in Chillicothe, halfway through, and spent most of my remaining cash to buy their last remaining pair of rain pants. I remember stopping in the restrooms of the food stops and taking my shoes and gloves off, running the electric hand dryers, trying to get some feeling (besides pain) back into my fingers and toes. I was completely beat down by the wind. Late in the day, a few merciful strong riders were going back and pulling pacelines back in, and I was able to join one of these. The ONLY reason I finished that ride was because I knew I'd never live it down with my friend if I quit.
When I got back on Sunday, it turned out that my very fair-skinned, Irish-descended friend had gotten a horrible sunburn on Saturday and had to drop out of the ride. 
But I still got my first TOSRV finish.
Speed comes from what you put behind you. - Judi Ketteler