I absolutely LOVE road tubeless. To me, the increase in comfort and grip through using lower tire pressure is 100% worth it. And having done it once or twice, I now find it pretty easy. I’m using 30mm Schwalbe G-One Speeds. They have been great, even over very rough road surfaces and slamming into potholes that should make a LandRover cry. Just placed an order for a set of Schwalbe Pro One’s for summer use (hopefully on better roads).
A couple of tips:
– Whatever your problem is, it’s probably the rim tape. And if you’re sure it isn’t the rim tape, then it DEFINITELY is the rim tape. Don’t ask me how I know that. 


– I’m not a huge fan of Stan’s rim tape. It’s fine, but I like the DT Swiss rim tape better. Feels thicker and slightly easier to work with.
– I always do two layers of rim tape. Really make sure it’s flat and there are no bubbles.
– I second what someone said above: air escaping around the valve stem probably isn’t the valve: it’s the rim tape. [I TOLD YOU NOT TO ASK ME HOW I KNOW THAT!!!]
– That said, I have had issues with valves as well. Basically, I was convinced there was a leak from a valve stem not sealing properly (it was a Milkit valve), so I kept cranking down on the valve nut…until I managed to pull the conical plug from the bottom of the valve into the cavity of the rim itself. I’ve since switch to the Orange Seal valves and I absolutely adore them. They come in a great kit with everything you need. They include two types of rubber gaskets for the bottom of the valve. One is elongated, the other is conical. For my wheels (HED Ardennes), the elongated once fits perfectly into the rim channel. This prevents the valve from twisting when cranking down on the nut, or when installing and removing valve cores. If the elongated one doesn’t fit, the conical one will. And it is big and burly enough to not slip into the rim cavity.
– For mounting tires the first time, I can also recommend the Kool Stop Tire Bead Jack linked to above. It isn’t perfect, but it is useful and worth the money.
– I always use a bit of soapy water when first mounting the tires. You don’t need much. Only takes a second and is very helpful.
– I use an Airshot. Useful thing. Cheaper than a compressor or air tank (which it effectively is). But I recently bought a dedicated high volume pump for fat MTB tires, and that seems to work quite well, too.
– I inflate my tires, get the beads to pop into place, then inflate to 80 psi and wait a few hours. If the tires are holding most of the air, then I remove the valve cores and install the sealant through the valve. Works well. When installing sealant, I like to hang my wheels so the valve core is at 4 o’clock or 8 o’clock. That lets the sealant run down into the tire and helps to avoid sealant “backing up” and spilling out of the valve.
– Before installing a valve core, I dip it in sealant.
– When changing tires, I again hang the wheels with the valves at 4 or 8 o’clock, then release the air from the tire through the valve. (Hanging the wheel so the valves are slanted down allows the sealant to drain from the valve before you release the air. Otherwise your valve will spray sealant.) I then hang the wheels with the valves at 6 o’clock. Using the plunger and syringe assembly from a Milkit kit (love the system, but hate the valves), I suck out all the sealant. (Hanging the wheels with the valves at the bottom makes it easy to put the syringe straight in to capture the sealant at the bottom of the tire.) Then I can pop the bead on the tire and clear out any removing sealant with paper towel. No mess, no fuss.
Well, this is already too long, but those are my tips on road tubeless. (Shameless plug: I can’t speak highly enough about the Schwalbe G-One Speeds. Great tires.)
Best,
Adam