Welcome! I am also a cyclist, and I have been interested in hammocks simply for their packability. I will try to answer your questions, and also offer some suggestions...
1. I made all my own hammocks so far, so I can't give you advice on a company.
2. Your shoulder is something I think may be an issue if this is a mountain biking trip you are embarking on. I rode Steamboat Springs to Salida on the Great Divide Route, and I was very surprised at the abuse my hands, arms, and shoulders recieved on the off road decents.
If you are getting upper body pain while riding your bikes, I suggest you look into recumbents. I am riding one now primarily, and there is zero pressure on my hands and arms. All the weight is going into the foam seat and the mesh backrest.
But, you are asking about hammocking, and your shoulder. Well, all I can say is if you are waking up after sleeping on the ground and feeling pain, I would look into hammocking for sure. I have always been a trooper, and never complained too much about sleeping on the ground, but when I get into my hammock, it is a whole other ball game. I have literally dozed off within minutes while testing without even noticing I was falling asleep!
3. I have no experience setting up a bivy with my hammock. I think you are referring to the Hennessey setup. I think you could use the bike as a pole by backtying it. Finding just one more place to tie-off should be relatively easy.
Quite a few here have said that the stock tarp that comes with a HH is too small, and from looking at it, I agree. It wouldn't be for me. And when the clouds open up and the storm starts swirling you would want to be as covered as possible. IMO, the idea of bivying up my hammock while using a small tarp like that in a tent mode that is barely covering you is no good.
4. There is a system by Speer called the Segmented Pad Extender. I feel it looks really funky, but people have really liked theirs.
Speer Hammocks Segmented Pad Extenders! This would also cover your need to go to ground.
If I had a bad injury I would probably not be mountain biking. But, you Colorado folk are really crazy for your mountains! And, we Kansans are very jelous!
So, I guess if you are going to go, I would think the hammock is likely to rejouvenate you better than sleeping on the ground.
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