Assuming you take to the MBB format, especially on a V20, and there aren't any physical limitations in riding it, I think you will grow to love it. For long distance touring it is a very heavy puncher IMO, especially on the flattish stuff. Not to take anything away from its hill climbing ability, which it can climb, but some people dismiss it for what is not its forte. Kinda like those who say Ferraris or Lamborghinis suck because they are not as easy to parallel park as a Prius.
As a first recumbent, making the jump straight into a V20 is doable. I made the switch after almost 2 straight years in the TT position so my brain took a bit longer to rewire the balance than most people, so I was weaving all over the place for about 2 weeks before being able to keep it upright reliably. A friend made two trips across a small parking lot. The first was Flintstoning, and the 2nd one was with his feet on pedals.
1. Hills - Some people assume that once a recumbent hits a hill then it is game over, which is not the case at all. Assuming you have legs to get up hills on a road bike already you should be able to get up them on a V20 as well. It might take a bit longer depending on how steep they are, but you'll surely be able to make up for lost time on the descents and flats. A member crunched the relevant numbers between me on my road bike and me on my V20, and came up with the approximate break-even points with my then 250 watt FTP. I attribute this more to a weight issue (16kg vs 8kg bike weights) than anything else but I was able to get my V20 FTP up to 257, whereas my best ever on a road bike was only 247. This kind of casts doubt (at least in my case) that riders are going to take a hit on the watts when making the switch.
Steeper favored the road bike due mostly to the weight, and favored the V20 for anything flatter or descending.
250 watts on both = speeds were the same at about 2.5% grade.
175 watts on both = speeds were the same at about 2% grade.
125 watts on both = speeds were the same at about 1.5% grade.
Based on those numbers I guestimated that for the speeds to be the same at about a 3% grade I would need about 300 watts, maybe 325 to not get dropped. Maybe not very useful for randonneuring, but it's a starting point.
3. Gear/bags/hydration. I use a 3L Osprey hydration bag inside a North Face 6L joggers bag worn backwards on my chest with a drink tube. On hot days I add varying amounts of ice to keep me cool, and add a powdered mix (like Gatorade) to taste.
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Hands free drinking, excellent for cooling with a lot of ice, has a little spare room for cell phone, chapstick, snacks and easy to access without stopping.
As for why I switched, the 2 main reasons are speed and comfort. Neck pain had me hating to get on my upright bikes, and the butt/back/hand pain surely made the choice much easier. On my best day I could handle 4 hours on it before discomfort forced me to take breaks even though my legs still had plenty of life in them. Since getting my V20 I have numerous days with 7+ hours nonstop, and the only real reason I got off when I did was boredom and I ran out of hydration/food. I was just starting to get recumbutt near the end, but it certainly wasnt discomfort that caused me to get off.