@FTlatheworks I'm sure that there are two factors causing your problem, but I'd love to be near to test them out. I really like to measure these things for myself, not because I don't trust anybody, but as I measure in person I might notice things sometimes missed by other guys.
One factor is that the tailstock isn't perfectly flat, as you alluded to above (this is easier to fix than you might imagine). The second is that there are inclusions in the casting that contain carbides - all grey iron contains carbides, but there is a tendency for carbide clusters to be created near inclusions that contain excess carbon.
By taking a flat stone and lightly stoning the tailstock surfaces, you might very well discover one or more of these areas. This thing isn't directly Matt's problem at PM or at the factory. When I refurbish 80 year old 'best of breed' machines I have to be careful of this as I rebuild them. If you find one, take a diamond hone and relieve it. even if you go a little too far, it won't hurt your tailstock, and will eventually result in wider contact area. Even if it doesn't, you should still be okay.
Note that a few scratches isn't harmful to you lathe bed. They will even hold a little oil which can be beneficial - they just look bad.
WRT to the shape, each shape, (convex, concave or random) has a different strategy that I'm sure
@Richard King 2 can give you some pointers about, but that is a very long post indeed. It isn't rocket science, but the strategy has to be appropriate to the situation.
P.S. Taking a stone to the tailstock finish will help take out any sharp peaks, will make the movement feel smoother anyway.