I've not mounted the Homage, but I've mounted a wide array of tires to Cliffhangers, both in 26 and 650b. Wire bead tires are fairly easy to mount, especially with the depth of the well and the amount of internal space. A bit harder time than I've had with other rims, but not so bad. Tight-fitting tubeless tires can be quite difficult to mount, especially when brand new, and especially with the use of a tube. I probably spent a solid hour mounting WTB Byways, broke at least one tire lever, and worried I was using so much force I was going to damage the rim, but it ended up working out. However, with these tighter fits, I've found them quite easy to set up tubeless.
I recently mounted some Race Kings and the fit was so tight they held air overnight before I added any sealant. I also find it easier to use a tube to get things seated. I mount the tire normally with a tube, check for proper seating, then leave it for a while pumped around max PSI, usually just trying to get the weirdness out where they were folded up in the packaging. Sometimes it takes a few days of riding. I then deflate and remove the tube while leaving one side seated. Once it's out, I mount the valve, push the side I opened back into the well, give it a strong blast of air, and it usually pops right back into place. I've found it easiest to add sealant through the valve (removable cores), versus pouring it into the unmounted tire.
With all this said, my experience tells me the Cliffhangers offer a solid, tight fit for all the tires I've mounted. If you can get the simworks tires to hold air without a tube, then I reckon you're halfway there. I'm not sure of the safety of running standard tires tubeless, but I've read plenty of stories about people's tubeless-compatible RH tires blowing off the rim, so I'd bet it's no more dangerous than that.
re: the Rene Herse/tube advice - they offer a lot of wisdom, but I try to take everything they say with a grain of salt, remembering their primary goal is to sell products. Despite their recommendations for their tires, I don't think you can go wrong buying the "right size" tubes for the right size tires. Sure, tubes do stretch, and it should work in theory, but I'm not counting grams and I don't quite see the benefit of undersizing tubes beyond that. The manufacturers have already done the work for me, spec'ing tubes for tires, so I'm not going out of my way to try and outsmart them.
Good luck with the tires! I hope you're able to get them mounted up.
-J.C.