It really depends on what you want in a bike.
I grew up teaching myself about mechanics on classic cars, hated the modern stuff. Then I put myself through college as a mechanic and starting working in the industry. Nearly 3 decades later (most of which spent writing repair manuals, the last ~7 years writing motorcycle repair manuals) - I DON'T HAVE ANY TIME/INTEREST in my life for an antique bike.
I understand them, I get the appeal, I don't like most things about them especially many of the maintenance aspects.
I have a young family and I spend my time with them sneaking off for rides when I can. I don't want to be spending time in the garage a second more than I have to so oil changes and valve adjustments are fine with me, but that's it man. I want to turn the key and go.
Even my Cali Jackal which was a fantastic bike in a lot of ways was too fiddly. I'm not even looking for spoke wheels or a sump I have to drop when changing the oil.
Now some comment on the "feel" of a big block, and there's a difference. Though it almost sounded like some were not just talking about the motor but meant the perception of build quality from the "feel" of the components. I poo poo that. It's a real PERCEPTION sometimes, but that doesn't make it a reality.
Now I'm just gonna mention it one more time because I really think it's the unicorn in the discussion IF you're looking for a modern Guzzi that FEELS like a big block and has relatively neutral upright riding position - THE FIRST GENERATION V9. The motor FELT every bit like my big blocks (which coming off owning a V7 for a while at that point literally shocked me). I didn't expect to like it, never mind fall in love with it.
If I were looking for what you said you were, THAT would be MY first stop (because of the all other modern amenities). Worst case scenario I swap on a v7 tank eventually for the looks.
Other thoughts mentioned in this thread - V100 Cali - NOPE - no way it will be small enough even if they make it.
Triumph Bobber - not a bad one, considered it myself. Motor feel will be different but I'm sure it's a fine bike.
That new RE - damn that's actually a pretty fine looking bike - it's not for me though, and offers nothing that I can't get in a Guzzi V9 or V7 (not to mention doesn't offer some of the same advantages I find in the Guzzi).
But that's all about ME - my perspectives on a bike. You just gotta find yours. If you have the time for it and don't mind spending double, then yeah maybe an antique original with greatly upgraded running gear might be the answer for you - it sure as hell isn't for me.
Good luck...
I'm sticking with my modern smallblocks for the foreseeable future:
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