I don't have specific experiences in trading up or down but your post made me think about one specific problem with your proposed approach (this is something I think a lot about lately as well): Basically, that card appreciation is non linear by grade.
The PSA 7 and PSA 1 versions of X card don't go up at the same rate. So...by purchasing the 1 now, you aren't in lockstep with that PSA4-7 in someone else's possession. The amount of money you will need to bridge that gap in the future will seem even more insurmountable.
I don't have any data handy to back this up, and I don't think this applies as much to pre war cards. So...grain of salt.
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