How Big is Too Big?

[Alsani]

I am getting ready to repot a couple of plants. The plants are relatively large and I was planning on separating them as best I can, however, my wife prefers to keep them as specimen plants (she really just doesn't want me overhandling them, fearing I will kill them. )

Anyway, I have a nicely growing cattleya that is getting too big for its 8-inch pot. There are at least half a dozen new pbulbs growing. I figure I will just transfer it into the next larger size but I do worry about having too much medium. Also, I haven't seen the roots on this plant so I don't know how compacted the current root system is. Any advice?

The second plant is a Sharry Baby growing in a slatted basket. As you can see from the pictures it seems to be growing upwards out of the basket. In fact, one side of the basket is fairly empty. 1) How do I remove it from the basket? Is this a good idea? The root system does seem to be fairly well intertwined. 2) Can I keep this as a single plant and repot in a larger/different container? Or is it better to separate into a couple of plants? Will it keep growing upwards or can I coerce it into growing outwards again.

Thanks all.