Craig spoke at the last Connecticut Surfcasters meeting and discussed/demonstrated the self service kit. While I will not comment on the price, he did answer many of the questions posted here. This is my take on things after his demonstration only so please do not take it as gospel.
My understanding is that the kit is for any VS that does not have the smooth sideplate. Those really old VS's should still be sent in for warantee. Also, once you have the kit you can purchase replacement lube and seals from your local service shop or from VS directly. Normal parts can be purchased directly from VS or a service center as always. I don't know why this would not apply to those that purchased a kit back when they used to sell it, but can not be sure. As to the oil, I am pretty sure they eliminated filling the reel with oil years ago. Oil only goes around the seals. When I bought my 250 around 2000 or so, I also picked up the self service kit. My reel came with grease only inside it. Not sure why people still think they are oil filled.
