I bought a pair of Heidenau K66s, which I really like. (I used this same tire on The Bride). In this case, I’m going with identical tires front and rear, 90/80-16. They’re on the small side for these rims (both 2.15″ wide), but with only 5 horsepower and a single drive ratio, I was aiming for lighter weight and smaller diameter.
I attempted to spoon the front tire onto the rim about a week ago, and for the life of me I couldn’t get the front tire (which is a tubeless rim) to seat on the bead. I wrestled with it for many hours. With a ratchet strap around it I could get it to inflate, but it just wouldn’t pop into place. I went as high as 70+ PSI, bonked it with a rubber mallet, and even upped my game from soapy water to Beadbuster commercial tire mounting lube.
None of it would do the trick. Look at the 1 o’clock to 3 o’clock position in this photo:

After three days of messing with it, I still couldn’t get the bead over the safety rib on the tubeless rim. I tried switching out tires in case the one I was trying to put on the front was defective. (Remember, the front and rear tires are identical.) I de-mounted it and switched tires.
On the front, I did all that again, with EXACTLY the same result. But I mounted the other tire on the tube type rear wheel and the bead popped at 85 psi. At that point, I had very little to lose. Once I had exhausted the alternatives and overcome my fear, I cranked the air compressor up to 120 psi and gave it a go without the valve stem in. It turns out the magic number was 110 PSI.
Great Success!

So, it worked out, right? Well, NO, not really. The rear tube I was received from Midwest Traction wan’t what I ordered. The one I got was too small (2.25″ tube for a 90/80 tire? Really?) and even though it held air for a while, the next day I heard a sudden woosh of air, and it went flat. So I will need to mess with the rear tire again, too.