Agree with Julian....Flying in cloud is no different to flying in clear skies, just you see less. As long as you know what you're doing then whats the problem.
To answer your questions:
1) yes
2) if someone wants to come along for the ride then thats fine. If they don't then thats fine also .
On the subject of 2 vacuum pumps, and something to bear in mind....was flying a Seneca which for obvious reasons has two vacuum pumps. One failed and although theoretically everything should have been just dandy on one pump, it wasn't.....
Cheers
EA