Jaimee - there's a couple of possibilities there. In the second pic she looks like a classic roan with some appaloosa pattern (the spotty skin would suggest that). Although you say she never changed colour, there's a lot mroe roaning on the second pic than on the first. If that was a seasonal change then that too would suggest classic roan. If however she did get more roaned as she got older, then the pattern is failry typical of varnish roan (unusual to see so little roaning on the head with varnish roan though).
The other possibility is rabicano. Rabicano causes 'skunk' tail - where there's white striping and roaning on the dock and the quarters - the first pic is quite typical of that. The white tail, heavily roaned quarters and darker shoulder and head is very rabicano.
Without knowing her breeding or being able to see pics of her as a foal and yearling it's almost impossible to say for sure.
cvb - Gelfy is I'm afraid an unknown as far as breeding goes. In some ways he looks sec C ish, maybe crossed with short cobby type or something, but to be honest, he could have anything in there (and probably does!). Your Eriskay will eventually go white - as do all greys who live long enough! It's difficult to say how quickly she'll grey out - some ponies are white by the age of four (as May was) while others seem to retain a fair bit of pigment into their teens. Gelfy is getting whiter very quickly now - I think by his early teens he will be pretty much white all over. What you'll find is that she'll get paler each time she sheds out her coat; so each winter and summer coat will be progressively whiter each year.
HC - That's another odd one - fleabitten markings do vary quite a lot. Some horses get none at all - some get so many they look almost roaned from a distance. It's not uncommon to see what's called 'bloody shoulders' on Arabs - kind of like freckles that are so concentrated they look like roan patches.
It seems that in some greys, the process by which pigment is no longer produced in the hair follicle is reversed to an extent; she won't get spotty as such, or end up solid coloured again, but most horses that do develop freckles develop a lot of them if they live long enough.