I've always loved that question, "what's it worth?" as the answer is always "whatever someone is willing to pay for it".
I'm not sure all real wealthy buys who own gen 1 want a gen 2 though. I personally just don't like the look of the gen 2. I'm wasting my car money these days on fancy SUV's over getting a gen 2.
I'd still consider a black gen 1 2014-2015 unmodified v10 car with lower Mike's and diamond stitched seats, but have not seen one come up at a decent price. There is one in Boston McLaren but they want like 130k and fidelity warranty was like 10k on top of that. Seems stupid for a bit faster car with a bit lower miles than mine
I'm in that boat. I'm fortunate to be able to afford pretty much whatever I'd want to drive, but I'm really picky about cars. I need to love it. I've now had the R8 for about 9 years, and it's the longest I've ever owned any car. I enjoy and value it more today than when I bought it. While the Gen-2 has improved performance, I just didn't like the look of it when it came out. It's grown on me a bit more since, but it's never been a car I lusted after like the Gen-1.
What's going on with the market? I don't know, I honestly don't track it... aside from a periodic inspection for the sake of a thread like this. But this car is an icon, and time will serve it well. At some point, not far from now, I think you'll find a feeding frenzy because there just aren't many cars out there with 10 or 12 cylinders, naturally aspirated, high revving, in such a complete package... and many are just waking up to the fact that what's built is the end of the line. You'll have hybrid drivetrains for a short while (most with smaller displacement) and then soul-crushing electric.
Nonetheless, I wouldn't get hung up on the market. Be glad you own one and drive it. I enjoy mine every chance I get - which is less often than I'd like. Who knows what the future holds, but now's the time to enjoy it. It's not an investment, but a toy... track the stock market, but drive your R8.