Sometimes the valve guides have sharp edges. I usually smooth them down with sandpaper if they feel sharp and use a LOT of oil to lube the seals before installing them. The bottom line is, yes, you can screw up the install by damaging the seal. It's not as difficult to do as you'd think.
Replace the leaking seal again, don't bother trying to test it; they are cheap and I am not sure it is possible to test anyway. Excess oil on the valve should be evidence enough, but it is also possible that there is too much play in the guide.
Hopefully you put each valve back on the same side of the engine it came from originally.
In regard to the guides:
You'll want a machine shop to work on the guides; they'll bore them out and sleeve them. Typically they aren't replaced. Last I checked it wasn't terribly expensive to do. I'm not sure what is involved on the valve side of the job or whether they can fix your existing valves or whether they'd have to be replaced, but I think you can keep them.