Hmm, I tend to see the 2 of Pentacles as (literally, if using RWS imagery) juggling two actual possibilities, things, events. Someone dividing time on two jobs would be an example.
With the Page of Swords, there's a less active quality. This is more about being ready to react to whatever comes your way, than going out there and involving yourself.
The Page is wary and ready to strike. The 2 of Pents has a bit more fun with whatever the situation is - there is little suspicion involved, whereas the Page keeps things and people at a distance.
Another way to approach this is to relate the Page to thoughts, and the 2 to actions. As you say, there are some simiarities present, but the two outlooks represented are quite distinct from each other.
If a there a problem to solve, the 2 of Pentacles would get to it, while the Page would examine it first in an attempt to find the weakest spot for attack.