So I saw that you mentioned your Masi, and I did a quick search through the old threads and confirmed my hunch that I responded to your thread/questions about the Masi Giramondo back in early 2019. So did you pick up a Giramondo? It's a great, fun and very versatile bike....and that is the bike that i'm running the RH tires on. At some point in the future when you might want to try a second wheelset, pick up a 650b set and give the Road+ thing a try...it works really well on the Giramondo and gives it a different personality. There is a blogger guy who posted a long review of the Giramondo a couple of years ago, and he also had great things to say about the Giramondo running 650b Road+ tires, which generally means in the 48-50mm width.
I predict you will love the Supreme tires in general, but most definitely so in comparison to the Kendas. I am a bit of a geek when it comes to bike tires (and car tires as well), so I'm pretty familiar with the current Schwalbe line and have always admired the Supremes. I don't think you can go wrong with either version of the Supremes.
In our stable of 10 bikes or so (6 mine, 2 each for wife and daughter), we run Panaracer, Schwalbe, Continental, Clement/Donnelly, Specialized, Rene Herse and Rivendell tires (the latter 2 manufactured by Panaracer). They are all excellent in their own way. I do have a soft spot for Panaracer for a few reasons. They are willing to make low volume, ultra-cool tires for niche brands like Rene Herse, Rivendell, SOMA, etc. They actively support "obsolete" tire size like 27", 26", etc. with quality tires (I still ride 26" for mtb and use Panaracer exclusively for that bike at this point). Many of their tires are made in Japan to a very high quality standard. And my understanding is that they spend very little $ on marketing, etc., unlike bigger players like Conti, Schwalbe, etc. Good stuff IMO.
Re tubeless, I hear you. I am a holdout on tubeless and still run tubes on everything, including MTB. I have a few friends and know of a couple of touring friendly shop owners who are starting to push tubeless for touring. They feel that the technology is there, but they readily admit that for touring, you would still need to carry at least one tube, as well as other stuff. For me, the biggest issue is that I like to split my time riding different bikes. So the Giramondo gets used a fair amount when preparing for a tour and then on tour....and for short overnights in the Summer, but there are times when she hangs in the garage for a couple of months while I ride other bikes. My lingering impression is that tubeless is a PITA in that situation, and requires more periodic care. I'm really not interested in that at this point. But I am keeping an open mind and I expect I will give it a try in the near future. The RH tires are tubeless ready as are the Velocity rims.
Good stuff. Hope you are hanging in there re the pandemic, all the best.
J