Howdy,
If you are trying to take advantage of the Winchester futures market, then buying anything else is counter-productive. Winchester makes a decent rifle, just not a great one any more. I would buy a Marlin long before I would buy a new model Henry... but that's just personal.
As for your Winchester dilemma, I would strongly suggest the .38-55 if you won't consider the .30-30. The .38-55 is a solid performer with modern ammunition, but like any cartridge that originated as a BP round, caution must be exercised when handloading. For your needs, the good ol' thuty-thuty is plenty fine, but it may not hold the cache you desire.
I would pass on the pistol length cartridges, as the 94 action was designed expressly for the longer rifle cases. However, all may be moot, as the continued buying pressure has made it difficult to find many choices when it comes to new Winchester 94s.
Adios,