Some thoughts:
Weight seems to be an issue stopping you from off-roading, so don't move from your 476lb V-Strom to another bike in the same weight class (460lb Transalp, 450lb T7, 460lb KLR650, 474lb Tiger 800Xcx). A 25lb weight loss is negligible and will do nothing to ease your trepidation, no matter how much more travel suspension or ground clearance you're going to gain. If anything, the increased seat height will make you more fearful of venturing off the pavement.
I think you should try to learn dirt on a much lighter bike. Don't worry about tubed/tubeless, cruise control, etc. right now. Focus on skills development and comfort. Take a lesson at
TrailTours or Clinton Smout's
Smart Performance Centre.
If you can afford it, pick up a much smaller dirt-oriented thumper dual-sport, like a WR250, CRF300L, KLX300, 250 XCF to learn on. These bikes are in a totally different weight class (ranging from 250-325lbs) and will make you feel much more comfortable in the loose stuff. Picking the bike up when you inevitably drop it will not be an issue, especially when you are riding solo. These bikes also survive drops a lot better than big-bore, multi-cylinder adventure bikes, not incurring as much damage or costing $$$ to fix in the event of an off. All this leads to much better learning environment as you push the envelope of your comfort level instead of always being scared of dropping your heavy, expensive adventure bike.
These off-road riding skills that you're building are 100% transferable from small bikes to larger bikes. You can go back and forth from your thumper to your V-Strom to measure your progress and try new skills that you've picked up on the smaller bike. This will also educate your butt on what makes a motorcycle good off-road as you move back and forth from a dirt-bike-oriented suspension to a street-biased one. When you go shopping for your next big-bike, you will know exactly what to look for on your test ride.
What this will eventually lead to is your ability to take much larger bikes off-road, which will also provide a more comfortable ride on pavement. I have much more confidence riding my 550lb R1250GS in dirt because of the time I spent learning on a 250lb enduro. Being comfortable on a larger, heavier bike will open your shopping list up to motorcycles that will also have the technologies you're looking for, like factory cruise control and cross-spoked wheels that terminate at the lip so you can run tubeless tires. Features that smaller bikes may not have as standard.
Speaking of, while you're at it, learn how to change an inner tube.
I know you're hesitant about going tubed, but the BDRs you are aspiring to ride carry a high risk of denting a rim, especially when you're a newb and you're not adept at making your front end lighter with the throttle to hop over rocks and obstacles that you can't easily avoid.
Denting a rim and losing air on a forest service road is not a critical event - you call CAA and they will come out and tow you out.
Denting a rim on the SoCal BDR means either fixing it yourself, or paying for a very expensive 4x4 rescue service to climb rocks to bring your bike out.
My buddy dented a rim on his 1290 Super Adventure R with tubeless wheels on the WABDR, which is considered to be one of the easiest BDRs to tackle. Like you, he thought his chances of denting a rim was low, so he didn't carry tubes or irons. Luckily I was, so we were able to get him out from the middle of nowhere back to civilization ourselves without calling for an expensive tow.
Tubes are not old technology. They are synonymous with off-road. I have dented rims on all my off-road bikes. It can even also happen on paved roads with potholes, especially when you are traveling through developing countries... or Quebec. Tubes also allow you to drop the air pressure to very low psi for increased grip in loose surfaces without risk of the tire unseating off the bead.
You can certainly run a tubeless tire for most of your travels so you're able to plug holes with an easy-to-use plug kit, but I'd always carry a tube and irons as a backup, so you can ride away from a dented rim when you are riding solo and out of cell service range with no one around to help you. Cultivating self-sufficiency in the event of *any* malfunction, no matter how low the odds are, is a critical skill when riding off-road solo.
There are other technologies like Tubliss and mousse which mitigate having to change a tube, but they come with their own disadvantages. Tubes are tried and true and are a universal fix all around the world. I had a puncture in India, a guy in straw hut nearby fixing kid's bicycles took off my wheel and tire and patched my tube for $0.50 while we went off and got a drink.
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